Substituted C-cyclohexylmethylamine derivatives

ABSTRACT

Substituted C-cyclohexylmethylamine derivatives, methods for the production thereof, pharmaceuticals containing said compounds, the use of substituted C-cyclohexylmethylamine derivatives for producing pharmaceuticals, and method of pain treatment using the pharmaceuticals.

CROSS REFERENCE TO RELATED APPLICATIONS

[0001] The present application is a continuation of International Patent Application No. PCT/EP01/11246, filed Sep. 28, 2001, designating the United States of America and published in German as WO 02/30870, the entire disclosure of which is incorporated herein by reference. Priority is claimed based on Federal Republic of Germany Patent Application No. 100 49 481.1, filed Sep. 29, 2000.

BACKGROUND AND SUMMARY OF THE INVENTION

[0002] The present invention relates to substituted C-cyclohexylmethylamine derivatives, to methods for their production, to pharmaceutical compositions containing these compounds and to the use of substituted C-cyclohexylmethylamine derivatives for producing pharmaceutical compositions.

[0003] The treatment of chronic and non-chronic pain conditions has great importance in medicine. There is a worldwide need for effective methods of treating pain. The urgent need for action for patient-friendly and purposeful treatment of chronic and non-chronic pain conditions, this being taken to mean the successful and satisfactory treatment of pain for the patient, is documented in the large number of scientific papers which have recently appeared in the field of applied analgesics and fundamental research work on nociception.

[0004] Conventional opioids, such as morphine, are extremely effective in the treatment of severe to the severest pain. However, their use is limited by the known side effects, for example respiratory depression, nausea, sedation, constipation and tolerance development. In addition, they are less effective in the event of neuropathic or incidental pain, from which patients with tumours suffer in particular.

[0005] An object forming the basis of the invention consisted in providing new analgesic substances which are capable of treating pain, in particular chronic and neuropathic pain.

DESCRIPTION OF THE INVENTION

[0006] The invention therefore relates to substituted C-cyclohexylmethylamine derivatives of formula I,

[0007] wherein

[0008] A is H; respectively singly or multiply substituted or unsubstituted aryl or heteroaryl;

[0009] R¹ is respectively saturated or unsaturated, branched or unbranched, singly or multiply substituted or unsubstituted C₁₋₁₀ alkyl or C₃₋₁₀ cycloalkyl; aryl, heteroaryl, aryl bound by saturated or unsaturated C₁₋₃ alkyl or C₁₋₃ alkylene or ethinyl; C₃₋₁₀ cycloalkyl bound by saturated or unsaturated C₁₋₃ alkyl or C₁₋₃ alkylene or ethinyl; or heteroaryl bound by saturated or unsaturated C₁₋₃ alkyl or C₁₋₃ alkylene or ethinyl, respectively unsubstituted or singly or multiply substituted by radicals, which independently of one another are

[0010] F, Cl, Br, I, OR¹⁸, SR¹⁸, SO₂R¹⁸, SO₂OR¹⁸, CN, COOR¹⁸, NR¹⁹R²⁰; unsubstituted or singly or multiply substituted C₁₋₁₀ alkyl, C₃₋₁₀ cycloalkyl or silyl; unsubstituted or singly or multiply substituted aryl or heteroaryl; or respectively unsubstituted or singly or multiply substituted aryl bound by saturated or unsaturated C₁₋₃ alkyl or C₁₋₃ alkylene, C₃₋₁₀ cycloalkyl or heteroaryl;

[0011] wherein R¹⁸ is H; saturated or unsaturated, branched or unbranched, unsubstituted or singly or multiply substituted C₁₋₁₀ alkyl or C₃₋₁₀ cycloalkyl; unsubstituted or singly or multiply substituted aryl or heteroaryl; or respectively unsubstituted or singly or multiply substituted aryl bound by saturated or unsaturated C₁₋₃ alkyl or C₁₋₃ alkylene, C₃₋₁₀ cycloalkyl or heteroaryl;

[0012] R¹⁹ and R²⁰, independent of one another, are H; respectively saturated or unsaturated, branched or unbranched, unsubstituted or singly or multiply substituted C₁₋₁₀ alkyl or C₃₋₁₀ cycloalkyl; unsubstituted or singly or multiply substituted aryl or heteroaryl; or respectively unsubstituted or singly or multiply substituted aryl bound by saturated or unsaturated C₁₋₃ alkyl or C₁₋₃ alkylene, C₃₋₁₀ cycloalkyl or heteroaryl;

[0013] or R¹⁹ and R²⁰ together form CH₂CH₂OCH₂CH₂, CH₂CH₂NR²¹CH₂CH₂ or (CH₂)₃₋₆, wherein R²¹ is H; unsubstituted or substituted phenyl; saturated or unsaturated, branched or unbranched, unsubstituted or singly or multiply substituted C₁₋₁₀ alkyl;

[0014] R² and R³ independently of one another are H; respectively saturated or unsaturated, branched or unbranched, singly or multiply substituted or unsubstituted C₁₋₁₀ alkyl or C₃₋₁₀ cycloalkyl; respectively singly or multiply substituted or unsubstituted aryl or heteroaryl; or respectively singly or multiply substituted or unsubstituted aryl bound by saturated or unsaturated C₁₋₃ alkyl or C₁₋₃ alkylene, C₃₋₁₀ cycloalkyl or heteroaryl;

[0015] or the radicals R² and R³ together represent CH₂CH₂OCH₂CH₂, CH₂CH₂NR⁶CH₂CH₂ or (CH₂)₃₋₆,

[0016] wherein R⁶ is H; respectively saturated or unsaturated, branched or unbranched, singly or multiply substituted or unsubstituted C₁₋₁₀ alkyl or C₃₋₁₀ cycloalkyl; respectively singly or multiply substituted or unsubstituted aryl or heteroaryl; or respectively singly or multiply substituted or unsubstituted aryl bound by saturated or unsaturated C₁₋₃ alkyl or C₁₋₃ alkylene, C₃₋₁₀ cycloalkyl or heteroaryl;

[0017] X in formula I has such a meaning that a part of formula I, as depectied in Partial Formula Ia,

[0018] partial formula Ia

[0019] has the following meanings

[0020] wherein B is OH, OR⁷, H, F, Cl or NR⁸R⁹,

[0021] wherein R⁷ is respectively saturated or unsaturated, branched or unbranched, singly or multiply substituted or unsubstituted C₁₋₁₀ alkyl or C₃₋₁₀ cycloalkyl; respectively singly or multiply substituted or unsubstituted aryl or heteroaryl; or respectively singly or multiply substituted or unsubstituted aryl bound by saturated or unsaturated C₁₋₃ alkyl or C₁₋₃ alkylene, C₃₋₁₀ cycloalkyl or heteroaryl;

[0022] R⁸ and R⁹ independently of one another are H; respectively saturated or unsaturated, branched or unbranched, singly or multiply substituted or unsubstituted C₁₋₁₀ alkyl or C₃₋₁₀ cycloalkyl; singly or multiply substituted or unsubstituted aryl or heteroaryl; or respectively singly or multiply substituted or unsubstituted aryl bound by saturated or unsaturated C₁₋₃ alkyl or C₁₋₃ alkylene, C₃₋₁₀ cycloalkyl or heteroaryl;

[0023] or R⁸ and R⁹ together form CH₂CH₂OCH₂CH₂, CH₂CH₂NR¹⁰CH₂CH₂ or (CH₂)₃₋₆,

[0024] wherein R¹⁰ is H; respectively saturated or unsaturated, branched or unbranched, singly or multiply substituted or unsubstituted C₁₋₁₀ alkyl or C₃₋₁₀ cycloalkyl; respectively singly or multiply substituted or unsubstituted aryl or heteroaryl; or respectively singly or multiply substituted or unsubstituted aryl bound by saturated or unsaturated C₁₋₃ alkyl or C₁₋₃ alkylene, C₃₋₁₀ cycloalkyl or heteroaryl, and

[0025]  is:

[0026] wherein R⁴ is H, COR⁵, SO₂R⁵; respectively saturated or unsaturated, branched or unbranched, singly or multiply substituted or unsubstituted C₁₋₁₀ alkyl or C₃₋₁₀ cycloalkyl; respectively singly or multiply substituted or unsubstituted aryl or heteroaryl; or respectively singly or multiply substituted or unsubstituted aryl bound by saturated or unsaturated C₁₋₃ alkyl or C₁₋₃ alkylene, C₃₋₁₀ cycloalkyl or heteroaryl,

[0027] wherein R⁵ is respectively saturated or unsaturated, branched or unbranched, singly or multiply substituted or unsubstituted C₁₋₁₀ alkyl or C₃₋₁₀ cycloalkyl; respectively singly or multiply substituted or unsubstituted aryl or heteroaryl; or respectively singly or multiply substituted or unsubstituted aryl bound by saturated or unsaturated C₁₋₃ alkyl or C₁₋₃ alkylene, C₃₋₁₀ cycloalkyl or heteroaryl,

[0028] wherein V is OR⁴ or NR⁴R¹¹,

[0029] wherein W is R¹¹, OR¹² or NR¹¹R¹²,

[0030] wherein R¹¹ and R¹² independently of one another are H; respectively saturated or unsaturated, branched or unbranched, singly or multiply substituted or unsubstituted C₇₋₁₀ alkyl or C₃₋₁₀ cycloalkyl; respectively singly or multiply substituted or unsubstituted aryl or heteroaryl; or respectively singly or multiply substituted or unsubstituted aryl bound by saturated or unsaturated C₁₋₃ alkyl or C₁₋₃ alkylene, C₃₋₁₀ cycloalkyl or heteroaryl,

[0031] optionally in the form of their racemates, their pure stereoisomers, in particular enantiomers or diastereomers, or in the form of mixtures of stereoisomers, in particular the enantiomers or diastereomers, in any mixing ratio; in the illustrated form or in the form of their acids or their bases or in the form of their salts, in particular physiologically acceptable salts, or in the form of their solvates, in particular the hydrates.

[0032] The compounds according to the invention exhibit outstanding analgesic properties.

[0033] In the context of this invention, alkyl and cycloalkyl radicals are taken to mean saturated and unsaturated (but not aromatic), branched, unbranched and cyclic hydrocarbons which may be unsubstituted or singly or multiply substituted. In this case C₁₋₂-alkyl represents C₁- or C₂-alkyl, C₁₋₃-alkyl represents C₁-, C₂- or C₃-alkyl, C₁₋₄-alkyl represents C₁-, C₂-, C₃- or C₄-alkyl, C₁₋₅-alkyl represents C₁-, C₂-, C₃-, C₄ or C₅-alkyl, C₁₋₆-alkyl represents C₁-, C₂-, C₃-, C₄-, C₅- or C₆-alkyl, C₁₋₇-alkyl represents C₁-, C₂-, C₃-, C₄-, C₅-, C₆- or C₇-alkyl, C₁₋₈-alkyl represents C₁-, C₂-, C₃-, C₄-, C₅-, C₆-, C₇ or C₈-alkyl, C₁₋₁₀-alkyl represents C₁-, C₂-, C₃-, C₄-, C₅-, C₆-, C₇-, C₈,- C₉- or C₁₀-alkyl and C₁₋₁₈-alkyl represents C₁-, C₂-, C₃-, C₄-, C₅-, C₆-, C₇-, C₈-, C₉-, C₁₀-, C₁₁-, C₁₂, C₁₃, C₁₄-, C₁₅-, C₁₆-, C₁₇- or C₁₈-alkyl. Furthermore, C₃₋₄-cycloalkyl represents C₃- or C₄-cycloalkyl, C₃₋₅-cycloalkyl represents C₃-, C₄- or C₅-cycloalkyl, C₃₋₆-cycloalkyl represents C₃-, C₄-, C₅- or C₆-cycloalkyl, C₃₋₇-cycloalkyl represents C₃-, C₄-, C₅-, C₆-or C₇-cycloalkyl, C₃₋₈-cycloalkyl represents C₃-, C₄-, C₅-, C₆-, C₇- or C₈-cycloalkyl, C₄₋₅-cycloalkyl represents C₄- or C₅-cycloalkyl, C₄₋₆-cycloalkyl represents C₄-, C₅- or C₆-cycloalkyl, C₄₋₇-cycloalkyl represents C₄-, C₅-, C₆- or C₇-cycloalkyl, C₅₋₆-cycloalkyl represents C₅- or C₆-cycloalkyl and C₅₋₇-cycloalkyl represents C₅-, C₆- or C₇-cycloalkyl. With respect to cycloalkyl, the term also comprises saturated cycloalkyls, in which one or two carbon atoms are replaced by a heteroatom, S, N or O. However, the term cycloalkyl also includes singly or multiply, preferably singly, unsaturated cycloalkyls without a heteroatom in the ring, if the cycloalkyl is not an aromatic system. The alkyl and cycloalkyl radicals are preferably ethyl, vinyl (ethenyl), propyl, allyl (2-propenyl), 1-propinyl, methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, hexyl, 1-methylpentyl, cyclopropyl, 2-methylyclopropyl, cyclopropylmethyl, cyclobutyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, cycloheptyl, cyclooctyl, but also adamantyl, CHF₂, CF₃ or CH₂OH and pyrazolinone, oxopyrazolinone, [1,4]dioxan or dioxolan.

[0034] In conjunction with alkyl and cycloalkyl—unless explicitly defined otherwise—the term substituted in the context of this invention is taken to mean the substitution of at least one (or more) hydrogen radical(s) by F, Cl, Br, I, NH₂, SH or OH, wherein “multiply substituted” or “substituted” with multiple substitution is taken to mean that the substitution is made both on different and on the same atoms multiply with the same or different substituents, for example threefold on the same carbon atom as in the case of CF₃ or at different points as in the case of —CH(OH)—CH═CH—CHCl₂. Particularly preferred substituents in this case are F, Cl and OH. With respect to cycloalkyl, the hydrogen radical can also be replaced by OC₁₋₃ alkyl or C₁₋₃ alkyl (singly or multiply substituted or unsubstituted respectively), in particular methyl, ethyl, n-propyl, i-propyl, CF₃, methoxy or ethoxy.

[0035] The term (CH₂)₃₋₆ is taken to mean —CH₂—CH₂—CH₂—, —CH₂—CH₂—CH₂—CH₂—, —CH₂—CH₂—CH₂—CH₂—CH₂— and —CH₂—CH₂—CH₂—CH₂—CH₂—CH₂—, (CH₂)₁₋₄ is taken to mean —CH₂—, —CH₂—CH₂—, —CH₂—CH₂—CH₂— and —CH₂—CH₂—CH₂—CH₂, (CH₂)₄₋₅ is taken to mean —CH₂—CH₂—CH₂—CH₂— and —CH₂—CH₂—CH₂—CH₂—CH₂— etc.

[0036] An aryl radical is taken to mean ring systems with at least one aromatic ring but without heteroatoms in any of the rings. Examples are phenyl, naphthyl, fluoroanthenyl, fluoroenyl, tetralinyl or indanyl, in particular 9H fluoroenyl or anthracenyl radicals which can be unsubstituted or singly or multiply substituted.

[0037] A heteroaryl radical is taken to mean heterocylic ring systems with at least one unsaturated ring which contain one or more heteroatoms selected from the group conisting of nitrogen, oxygen and sulphur and which can also be singly or multiply substituted. Examples of heteroaryls include furan, benzofuran, thiophene, benzothiophene, pyrrole, pyridine, pyrimidine, pyrazine, quinoline, isoquinoline, phthalazine, benzo[1,2,5]thiadiazole, benzothiazole, indole, benzotriazole, benzodioxolan, benzodioxan, carbazole, indole and quinazoline.

[0038] In conjunction with aryl and heteroaryl, substituted is taken to mean the substitution of the aryl or heteroaryl by R²³, OR²³ a halogen, preferably F and/or Cl, a CF₃, a CN, a NO₂, a NR²⁴R²⁵, a C₁₋₆-alkyl (saturated), a C₁₋₆-alkoxy, a C₃₋₈-cycloalkoxy, a C₃₋₈-cycloalkyl or a C₂₋₆-alkylene,

[0039] wherein the radical R²³ represents H, a C₁₋₁₀ alkyl, preferably a C₁₋₆ alkyl, an aryl or heteroaryl radical or an aryl or heteroaryl radical bound by C₁₋₃ alkyl, saturated or unsaturated, or a C₁₋₃ alkylene-goup-bound aryl or heteroaryl radical, wherein these aryl or heteroaryl radicals are not themselves substituted by aryl or heteroaryl radicals, and

[0040] the radicals R²⁴ and R²⁵, which are the same or different, represent H, a C₁₋₁₀ alkyl, preferably a C₁₋₆ alkyl, an aryl radical, a heteroaryl radical or an aryl or heteroaryl radical bound by saturated or unsaturated C₁₋₃ alkyl or a C₁₋₃ alkylene-goup-bound aryl or heteroaryl radical, wherein these aryl or heteroaryl radicals must not themselves be substituted by aryl or heteroaryl radicals,

[0041] or the radicals R²⁴ and R²⁵ together mean CH₂CH₂OCH₂CH₂, CH₂CH₂HR²⁶CH₂CH₂ or (CH₂)₃₋₆, and

[0042] wherein

[0043] the radical R²⁶ represents H, a C₁₋₁₀ alkyl, preferably a C₁₋₆ alkyl, an aryl radical, a heteroaryl radical or an aryl or heteroaryl radical bound by saturated or unsaturated C₁₋₃ alkyl or a C₁₋₃ alkylene-goup-bound aryl or heteroaryl radical, wherein these aryl or heteroaryl radicals must not themselves be substituted by aryl or heteroaryl radicals.

[0044] The term salt is taken to mean any form of the active ingredient according to the invention in which it assumes or is charged with an ionic form and is coupled to a counter ion (a cation or anion) or is in solution. This also includes complexes of the active ingredient with other molecules and ions, in particular complexes by ionic interactions.

[0045] The term physiologically acceptable salts with cations or bases is taken to mean, in the context of this invention, salts of at least one of the compounds according to the invention—usually a (deprotonated) acid—as anion with at least one, preferably inorganic, cation which are physiologically acceptable, in particular when applied to humans or other mammals. The salts of the alkaline and alkaline earth metals are preferred, but also with NH₄ ⁺, in particular however (mono) or (di) sodium, (mono) or (di) potassium, magnesium or calcium salts.

[0046] The term physiologically acceptable salts with anions or acids is taken to mean, in the context of this invention, salts of at least one of the compounds according to the invention—usually protonated, for example on nitrogen—as cation with at least one anion which are physiologically acceptable—in particular when applied to humans or other mammals. In the context of this invention this is taken to mean, in particular, the salt formed with a physiologically acceptable acid, namely salts of the respective active ingredient with inorganic or organic acids which are physiologically acceptable—in particular when applied to humans and/or mammals. Examples of physiologically acceptable salts of certain acids are salts of: hydrochloric acid, hydrobromic acid, sulphuric acid, methane sulphonic acid, formic acid, acetic acid, oxalic acid, succinic acid, malic acid, tartaric acid, mandelic acid, fumaric acid, lactic acid, citric acid, glutamic acid, 1,1-dioxo-1,2,dihydro-1λ⁶-benzo[d]isothiazol-3-on (saccharinic acid), monomethyl sebacic acid, 5-oxo-proline, hexane-1-sulphonic acid, nicotinic acid, 2-, 3- or 4-amino benzoic acid, 2,4,6-trimethyl-benzoic acid, a-lipoic acid, acetyl glycine, acetyl salicic acid, hippuric acid and/or aspartic acid. Hydrochloride salt is particularly preferred.

[0047] The analgesic tramadol has been successfully used for years in many countries to treat moderately severe to severe pain. Structurally derived from codeine and originally conceived as a cough mixture, it was found even in early tests that tramadol has a pronounced analgesic efficacy. Nowadays this is explained by the fact that the tramadol metabolite M1, which exhibits a clear affinity to the p subtype of the opiate receptor, is formed rapidly in vivo. However, in contrast to codeine or morphine, the participation of further mechanisms, the inhibition of symptosomatic noradrenaline and serotonin reabsorption could also be detected on the analgesic efficacy of tramadol (M. C. Frink et al, Arzneim.-Forsch/Drug Res. 46 (1996) 1029-1036; K. Flick et al, Arzneim.-Forsch/Drug Res. 28 (1978) 107-113). Despite this, according to current understanding the effect of M1 on the μ subtype of the opiate receptor is crucially responsible for the analgesic efficacy. The interaction of M1 with this receptor is comparable with that of morphine, i.e. in addition to the basic nitrogen atom, the phenolic OH group, which is methylated in codeine and tramadol, is crucial for binding to and activating the μ-opiate receptor which ultimately leads to analgesic effects.

[0048] Codeine (R═CH₃) Tramadol (R═CH₃)

[0049] Morphine (R═H) M1 (R═H)

[0050] In the mid 1990s it was found that a substituent in the 4-position of the cyclohexane ring of tramadol intensifies the analgesic efficacy. This applies not only to the 3-phenols but also to 3-thiophenols and prodrugs (I. Graudums et al, DE 19547766, Grüinenthal GmbH, 1995).

[0051] Compounds according to formula I are accordingly not part of this invention if

[0052] A is hydrogen,

[0053] R¹ is a phenyl ring, O- or S-substituted singly in the 3-position, and

[0054] R² and R³ are both methyl and

[0055] partial formula Ia has the following meaning:

[0056] in other words X represents

[0057] and B represents OH

[0058] and at the same time the grouping

[0059] is

[0060] wherein R⁴ is C₁₋₆ alkyl, C₂₋₆ alkenyl, C₅₋₇ cycloalkylmethyl, or substituted or unsubstituted phenyl or substituted or unsubstituted benzyl.

[0061] The compounds listed above are already known from DE 195 47 766 A1 (Graudums et al). However, as can be seen in formula I shown there, Grandums et al. assumed that, in principle, a phenyl ring O- or S-substituted singly in the 3-position is required for the analgesic effect, in particular for the μ-bond. This also coincides with the prevailing teaching as can be inferred, for example, from Chen, Z. R.; Irvine, R. J.; Somogyi, A. A.; Bochner, F. Life Sci. 1991, 48, 2165-2171.

[0062] It has surprisingly now been found in this invention that a phenyl ring O- or S-substituted singly in the 3 position is not a prerequisite for the p-bond and in particular analgesia.

[0063] Accordingly, this invention preferably relates to substituted C-cyclohexylmethylamine derivatives of formula I, in which R¹ is not a phenyl ring O- or S-substituted singly in the 3-position.

[0064] Also accordingly preferred are substituted C-cyclohexylmethylamine derivatives according to formula I, in which

[0065] R¹ is saturated or unsaturated, branched or unbranched, singly or multiply substituted or unsubstituted C₁₋₁₀ alkyl or C₃₋₁₀ cycloalkyl, preferably C₁₋₆ alkyl or C₃₋₆ cycloalkyl; naphthyl, heteroaryl, aryl bound by saturated or unsaturated C₁₋₃ alkyl or C₁₋₃ alkylene or ethinyl; or C₃₋₁₀ cycloalkyl, preferably C₃₋₆ cycloalkyl bound by saturated or unsaturated C₁₋₃ alkyl or C₁₋₃ alkylene or ethinyl or heteroaryl bound by saturated or unsaturated C₁₋₃ alkyl or C₁₋₃ alkylene or ethinyl, respectively unsubstituted or singly or multiply substituted by radicals selected independently of one another from

[0066] F, Cl, Br, I, OR¹⁸, SR¹⁸, SO₂R¹⁸, SO₂OR¹⁸, CN, COOR¹⁸, NR¹⁹R²⁰; unsubstituted or singly or multiply substituted C₁₋₁₀ alkyl, C₃₋₁₀ cycloalkyl preferably C₁₋₆ alkyl or C₃₋₆ cycloalkyl or silyl; unsubstituted or singly or multiply substituted aryl or heteroaryl; or respectively unsubstituted or singly or multiply substituted aryl bound by saturated or unsaturated C₁₋₃ alkyl or C₁₋₃ alkylene, C₃₋₁₀ cycloalkyl, preferably C₃₋₆ cycloalkyl or heteroaryl;

[0067] or R¹ corresponds to a compound according to formula II

[0068] wherein

[0069] R¹³, R¹⁵ and R¹⁷, independent of one another, are H, F, Cl, Br, I, OR¹⁸, SR¹⁸, SO₂R¹⁸, SO₂OR¹⁸, CN, COOR¹⁸, NR¹⁹R²⁰; saturated or unsaturated, branched or unbranched, singly or multiply substituted or unsubstituted C₁₋₁₀ alkyl, C₃₋₁₀ cycloalkyl, preferably C₁₋₆ alkyl or C₃₋₆ cycloalkyl or silyl; respectively singly or multiply substituted or unsubstituted aryl or heteroaryl; respectively singly or multiply substituted or unsubstituted aryl bound by saturated or unsaturated C₁₋₃ alkyl or C₁₋₃ alkylene or ethinyl, C₃₋₁₀ cycloalkyl, preferably C₃₋₆ cycloalkyl or heteroaryl;

[0070] R¹⁴ and R¹⁶, independent of one another, are H, F, Cl, Br, I, SO₂R¹⁸, SO₂OR¹⁸, CN, COOR¹⁸, NR¹⁹R²⁰; saturated or unsaturated, branched or unbranched, singly or multiply substituted or unsubstituted C₁₋₁₀ alkyl, C₃₋₁₀ cycloalkyl, preferably C₁₋₆ alkyl or C₃₋₆ cycloalkyl or silyl; respectively singly or multiply substituted or unsubstituted aryl or heteroaryl; respectively singly or multiply substituted or unsubstituted aryl bound by saturated or unsaturated C₁₋₃ alkyl or C₁₋₃ alkylene or ethinyl, C₁₋₁₀ cycloalkyl, preferably C₃₋₆ cycloalkyl or heteroaryl;

[0071] or R¹³ and R¹⁴, or R¹⁴ and R¹⁵ together respectively form the group OCH₂O, OCH₂CH₂O, CH═CHO, CH═C(CH₃)O or CH═CHNH, and R¹⁵—R¹⁷, or R¹³, R¹⁶ and R¹⁷ have the meaning given above,

[0072] wherein R¹⁸ is H, respectively saturated or unsaturated, branched or unbranched, unsubstituted or singly or multiply substituted C₁₋₁₀ alkyl or C₃₋₁₀ cycloalkyl, preferably C₁₋₆ alkyl or C₃₋₆ cycloalkyl; unsubstituted or singly or multiply substituted aryl or heteroaryl; or aryl, C₃₋₁₀ cycloalkyl, preferably C₃₋₆ cycloalkyl or heteroaryl; bound by saturated or unsaturated C₁₋₃ alkyl or C₁₋₃ alkylene, respectively unsubstituted or singly or multiply substituted;

[0073] R¹⁹ and R²⁰, independent of one another, are H, respectively saturated or unsaturated, branched or unbranched, unsubstituted or singly or multiply substituted C₁₋₁₀ alkyl or C₃₋₁₀ cycloalkyl, preferably C₁₋₆ alkyl or C₃₋₆ cycloalkyl; respectively unsubstituted or singly or multiply substituted aryl or heteroaryl; or respectively unsubstituted or singly or multiply substituted aryl bound by saturated or unsaturated C₁₋₃ alkyl or C₁₋₃ alkylene, C₃₋₁₀ cycloalkyl, preferably C₃₋₆ cycloalkyl or heteroaryl;

[0074] or R¹⁹ and R²⁰ together form CH₂CH₂OCH₂CH₂, CH₂CH₂NR²¹CH₂CH₂ or (CH₂)₃₋₆, wherein R²¹ is H, saturated or unsaturated, branched or unbranched, unsubstituted or singly or multiply substituted C₁₋₁₀ alkyl, preferably C₁₋₆ alkyl.

[0075] It was also assumed in DE 195 47 766 A1 (Graudums et al) that cyclohexanol is required for an analgesic effect. Surprisingly, however, this is not necessary, as the analgesic data of a series of compounds according to the invention show. Therefore, substituted C-cyclohexylmethylamine derivatives according to the invention are also preferred in which partial formula Ia is:

[0076] wherein B is OR⁷, H, F, Cl or NR⁸R⁹,

[0077] wherein R⁷ is respectively saturated or unsaturated, branched or unbranched, singly or multiply substituted or unsubstituted C₁₋₁₀ alkyl or C₃₋₁₀ cycloalkyl; respectively singly or multiply substituted or unsubstituted aryl or heteroaryl; or respectively singly or multiply substituted or unsubstituted aryl bound by saturated or unsaturated C₁₋₃ alkyl or C₁₋₃ alkylene, C₃₋₁₀ cycloalkyl or heteroaryl;

[0078] R⁸ and R⁹, independent of one another, are H; respectively saturated or unsaturated, branched or unbranched, singly or multiply substituted or unsubstituted C₁₋₁₀ alkyl or C₃₋₁₀ cycloalkyl; singly or multiply substituted or unsubstituted aryl or heteroaryl; or respectively singly or multiply substituted or unsubstituted aryl bound by saturated or unsaturated C₁₋₃ alkyl or C₁₋₃ alkylene, C₃₋₁₀ cycloalkyl or heteroaryl;

[0079] or R⁸ and R⁹ together form CH₂CH₂OCH₂CH₂, CH₂CH₂NR¹⁰CH₂CH₂ or (CH₂)₃₋₆, wherein R¹⁰ is H; respectively saturated or unsaturated, branched or unbranched, singly or multiply substituted or unsubstituted C₁₋₁₀ alkyl or C₃₋₁₀ cycloalkyl; respectively singly or multiply substituted or unsubstituted aryl or heteroaryl; or respectively singly or multiply substituted or unsubstituted aryl bound by saturated or unsaturated C₁₋₃ alkyl or C₁₋₃ alkylene, C₃₋₁₀ cycloalkyl or heteroaryl,

[0080] Surprisingly, substances according to the invention in which A is aryl or heteroaryl, singly or multiply substituted or unsubstituted respectively, exhibit a higher affinity with the α receptor than the compounds known, for example from DE 195 47 766 A1, where R¹ is a phenyl ring O- or S-substituted in the 3-position. Therefore, the compounds according to the present invention provide the possibility of reducing or completely avoiding side effects accompanying the binding to the μ-receptor.

[0081] However, the analgesic effect is obviously also a decisive criterion in this case, in particular in vivo.

[0082] A further preferred subject is C-cyclohexylmethylamine derivatives substituted according to the invention in which A is hydrogen. These are also new analgesics.

[0083] Compounds according to formula I are not a part of this invention if

[0084] R², R³, independent of one another, are

[0085] H, branched or unbranched, singly or multiply substituted or unsubstituted, saturated or unsaturated C₁-C₁₀ alkyl; saturated or unsaturated, singly or multiply substituted or unsubstituted C₃-C₇ cycloalkyl or a corresponding heterocycle, in which a carbon atom is replaced by N, S or O in the ring; saturated or unsaturated, singly or multiply substituted or unsubstituted alkylaryl or alkylheteroaryl; respectively singly or multiply substituted or unsubstituted aryl or heteroaryl; or

[0086] R² and R³ together form a ring and represent CH₂CH₂OCH₂CH₂, CH₂CH₂NR⁶CH₂CH₂ or (CH₂)₃₋₆;

[0087] X has the meaning that makes partial formula Ia to be:

[0088] in other words X represents,

[0089] A is hydrogen,

[0090] R¹ is an unsubstituted or singly or doubly substituted phenyl ring,

[0091] B is H, F, Cl, OH or OR⁷, wherein R⁷ is

[0092] branched or unbranched, singly or multiply substituted or unsubstituted, saturated or unsaturated C₁-C₁₀ alkyl; singly or multiply substituted or unsubstituted saturated or unsaturated C₃-C₇ cycloalkyl or a corresponding heterocycle, in which a carbon atom is replaced in the ring by N, S or O; saturated or unsaturated, singly or multiply substituted or unsubstituted alkylaryl or alkylheteroaryl; respectively singly or multiply substituted or unsubstituted aryl or heteroaryl;

[0093] and at the same time the group

[0094] represents

[0095] wherein V is OR⁴ wherein R⁴ is COR⁵ and wherein R⁵ is unsubstituted or singly or multiply substituted C₁₋₆ alkyl.

[0096] Compounds of this type are described in WO01/57232 A1 and are also found to some extent in Gais H. J., Griebel C. and Buschmann H., Tetrahedron: Asymmetry 11, 917-928 (2000).

[0097] According to the invention, it is preferred that R¹ is:

[0098] respectively saturated or unsaturated, branched or unbranched, singly or multiply substituted or unsubstituted C₁₋₁₀ alkyl or C₃₋₁₀ cycloalkyl, preferably C₁₋₆ alkyl or C₃₋₆ cycloalkyl; respectively unsubstituted or singly or multiply substituted naphthyl, heteroaryl, C₃₋₁₀ cycloalkyl, preferably C₃₋₆ cycloalkyl bound by saturated or unsaturated C₁₋₃ alkyl or C₁₋₃ alkylene or ethinyl or heteroaryl bound by saturated or unsaturated C₁₋₃ alkyl or C₁₋₃ alkylene or ethinyl;

[0099] and is substituted with radicals selected independently of one another from the group consisting of:

[0100] F, Cl, Br, I, OR¹⁸, SR¹⁸, SO₂R¹⁸, SO₂OR¹⁸, CN, COOR¹⁸, NR¹⁹R²⁰; unsubstituted or singly or multiply substituted C₁₋₁₀ alkyl, C₁₋₁₀ cycloalkyl, preferably C₁₋₆ alkyl or C₃₋₆ cycloalkyl or silyl; unsubstituted or singly or multiply substituted aryl or heteroaryl; and respectively unsubstituted or singly or multiply substituted aryl bound by saturated or unsaturated C₁₋₃ alkyl or C₁₋₃ alkylene, C₃₋₁₀ cycloalkyl, preferably C₃₋₆ cycloalkyl or heteroaryl.

[0101] It is also preferred that, in C-cyclohexylmethylamine derivatives substituted according to the invention,

[0102] R¹ corresponds to a compound according to formula II

[0103] wherein

[0104] R¹³, R¹⁵ and R¹⁷, independent of one another, are H, F, Cl, Br, I, OR¹⁸, SR¹⁸, SO₂R¹⁸, SO₂OR¹⁸, CN, COOR¹⁸, NR¹⁹R²⁰; saturated or unsaturated, branched or unbranched, singly or multiply substituted or unsubstituted C₁₋₁₀ alkyl, C₃₋₁₀ cycloalkyl, preferably C₁₋₆ alkyl or C₃₋₆ cycloalkyl or silyl; respectively singly or multiply substituted or unsubstituted aryl or heteroaryl; respectively singly or multiply substituted or unsubstituted aryl bound by saturated or unsaturated C₁₋₃ alkyl or C₁₋₃ alkylene or ethinyl, C₃₋₁₀ cycloalkyl, preferably C₃₋₆ cycloalkyl or heteroaryl;

[0105] R¹⁴ and R¹⁶, independent of one another, are H, F, Cl, Br, I, SO₂R¹⁸, SO₂OR¹⁸, CN, COOR¹⁸, NR¹⁹R²⁰; saturated or unsaturated, branched or unbranched, singly or multiply substituted or unsubstituted C₁₋₁₀ alkyl, C₃₋₁₀ cycloalkyl, preferably C₁₋₆ alkyl or C₃₋₆ cycloalkyl or silyl; respectively singly or multiply substituted or unsubstituted aryl or heteroaryl; respectively singly or multiply substituted or unsubstituted aryl bound by saturated or unsaturated C₁₋₃ alkyl or C₁₋₃ alkylene or ethinyl, C₃₋₁₀ cycloalkyl, preferably C₃₋₆ cycloalkyl or heteroaryl;

[0106] or R¹³ and R¹⁴ or R¹⁴ and R¹⁵ together respectively form the group OCH₂O, OCH₂CH₂O, CH═CHO, CH═C(CH₃)O or CH═CHNH and R¹⁵—R¹⁷ or R¹³, and R¹⁶ and R¹⁷ have the meaning given above,

[0107] wherein R¹⁸ is H; respectively saturated or unsaturated, branched or unbranched, unsubstituted or singly or multiply substituted C₁₋₁₀ alkyl or C₃₋₁₀ cycloalkyl, preferably C₁₋₆ alkyl or C₃₋₆ cycloalkyl; unsubstituted or singly or multiply substituted aryl or heteroaryl; or respectively unsubstituted or singly or multiply substituted aryl bound by saturated or unsaturated C₁₋₃ alkyl or C₁₋₃ alkylene, C₃₋₁₀ cycloalkyl, preferably C₃₋₆ cycloalkyl or heteroaryl;

[0108] R¹⁹ and R²⁰, independent of one another, are H, respectively saturated or unsaturated, branched or unbranched, unsubstituted or singly or multiply substituted C₁₋₁₀ alkyl or C₃₋₁₀ cycloalkyl, preferably C₁₋₆ alkyl or C₃₋₆ cycloalkyl; respectively unsubstituted or singly or multiply substituted aryl or heteroaryl; or respectively unsubstituted or singly or multiply substituted aryl bound by saturated or unsaturated C₁₋₃ alkyl or C₁₋₃ alkylene, C₃₋₁₀ cycloalkyl, preferably C₃₋₆ cycloalkyl or heteroaryl;

[0109] or R¹⁹ and R²⁰ together form CH₂CH₂OCH₂CH₂, CH₂CH₂NR²¹CH₂CH₂ or (CH₂)₃₋₆,

[0110] wherein R²¹ is H, C₁₋₁₀ alkyl, preferably saturated or unsaturated, branched or unbranched, unsubstituted or singly or multiply substituted C₁₋₆ alkyl, and

[0111]  is:

[0112] wherein R⁴ is H, COR^(5a), SO₂R⁵; respectively saturated or unsaturated, branched or unbranched, singly or multiply substituted or unsubstituted C₁₋₁₀ alkyl or C₃₋₁₀ cycloalkyl; respectively singly or multiply substituted or unsubstituted aryl or heteroaryl; or respectively singly or multiply substituted or unsubstituted aryl bound by saturated or unsaturated C₁₋₃ alkyl or C₁₋₃ alkylene, C₃₋₁₀ cycloalkyl or heteroaryl,

[0113] wherein R⁵ is respectively saturated or unsaturated, branched or unbranched, singly or multiply substituted or unsubstituted C₁₋₁₀ alkyl or C₃₋₁₀ cycloalkyl; respectively singly or multiply substituted or unsubstituted aryl or heteroaryl; or respectively singly or multiply substituted or unsubstituted aryl bound by saturated or unsaturated C₁₋₃ alkyl or C₁₋₃ alkylene, C₃₋₁₀ cycloalkyl or heteroaryl,

[0114] wherein R^(5a) is saturated or unsaturated, branched or unbranched, singly or multiply substituted or unsubstituted C₃₋₁₀ cycloalkyl; respectively singly or multiply substituted or unsubstituted aryl or heteroaryl; or respectively singly or multiply substituted or unsubstituted aryl bound by saturated or unsaturated C₁₋₃ alkyl or C₁₋₃ alkylene, C₃₋₁₀ cycloalkyl or heteroaryl,

[0115] wherein V is OR⁴ or NR⁴R¹¹,

[0116] wherein W is R¹¹, OR¹² or NR¹¹R¹²,

[0117] wherein R¹¹ and R¹², independent of one another, are H; respectively saturated or unsaturated, branched or unbranched, singly or multiply substituted or unsubstituted C₇₋₁₀ alkyl or C₃₋₁₀ cycloalkyl; respectively singly or multiply substituted or unsubstituted aryl or heteroaryl; or respectively singly or multiply substituted or unsubstituted aryl bound by saturated or unsaturated C₁₋₃ alkyl or C₁₋₃ alkylene, C₃₋₁₀ cycloalkyl or heteroaryl.

[0118] C-cyclohexylmethylamine derivatives substituted according to the invention are also particularly preferred, in which

[0119] R² and R³, independent of one another, are H; saturated or unsaturated, branched or unbranched, singly or multiply substituted or unsubstituted C₁₋₆ alkyl or C₃₋₆ cycloalkyl; respectively singly or multiply substituted or unsubstituted aryl or heteroaryl; or respectively singly or multiply substituted or unsubstituted aryl bound by saturated or unsaturated C₁₋₃ alkyl or C₁₋₃ alkylene, C₃₋₆ cycloalkyl or heteroaryl, or the radicals R² and R³ together form CH₂CH₂OCH₂CH₂, CH₂CH₂NR⁶CH₂CH₂ or (CH₂)₃₋₆,

[0120] wherein R⁶ is H; respectively saturated or unsaturated, branched or unbranched, singly or multiply substituted or unsubstituted C₁₋₆ alkyl, in particular CH₃, or C₃₋₆ cycloalkyl; respectively singly or multiply substituted or unsubstituted aryl or heteroaryl; or respectively singly or multiply substituted or unsubstituted aryl bound by saturated or unsaturated C₁₋₃ alkyl or C₁₋₃ alkylene, C₃₋₆ cycloalkyl or heteroaryl; and/or

[0121] R⁷ is respectively saturated or unsaturated, branched or unbranched singly or multiply substituted or unsubstituted C₁₋₆ alkyl, or C₃₋₆ cycloalkyl; respectively singly or multiply substituted or unsubstituted aryl or heteroaryl; or respectively singly or multiply substituted or unsubstituted aryl bound by saturated or unsaturated C₁₋₃ alkyl or C₁₋₃ alkylene, C₃₋₆ cycloalkyl or heteroaryl; and/or

[0122] R⁸ and R⁹, independent of one another, are H; respectively saturated or unsaturated, branched or unbranched, singly or multiply substituted or unsubstituted C₁₋₆ alkyl or C₃₋₆ cycloalkyl; respectively singly or multiply substituted or unsubstituted aryl or heteroaryl; or respectively singly or multiply substituted or unsubstituted aryl bound by saturated or unsaturated C₁₋₃ alkyl or C₁₋₃ alkylene, C₃₋₆ cycloalkyl or heteroaryl; or R² and R³ together form CH₂CH₂OCH₂CH₂, CH₂CH₂NR¹⁰CH₂CH₂ or (CH₂)₃₋₆, wherein R¹⁰ is H; respectively saturated or unsaturated, branched or unbranched singly or multiply substituted or unsubstituted C₁₋₆ alkyl or C₃₋₆ cycloalkyl; respectively singly or multiply substituted or unsubstituted aryl or heteroaryl; or respectively singly or multiply substituted or unsubstituted aryl bound by saturated or unsaturated C₁₋₃ alkyl or C₁₋₃ alkylene, C₃₋₆ cycloalkyl or heteroaryl, and/or

[0123] R⁴ is H, COR⁵, SO₂R⁵; respectively saturated or unsaturated, branched or unbranched singly or multiply substituted or unsubstituted C₁₋₆ alkyl or C₃₋₆ cycloalkyl; respectively singly or multiply substituted or unsubstituted aryl or heteroaryl; or respectively singly or multiply substituted or unsubstituted aryl bound by saturated or unsaturated C₁₋₃ alkyl or C₁₋₃ alkylene, C₃₋₆ cycloalkyl or heteroaryl,

[0124] wherein R⁵ is singly or multiply substituted or unsubstituted C₁₋₆ alkyl; respectively singly or multiply substituted or unsubstituted aryl or heteroaryl; or respectively singly or multiply substituted or unsubstituted aryl bound by saturated or unsaturated C₁₋₃ alkyl or C₁₋₃ alkylene, or heteroaryl, and/or

[0125] R¹¹ and R¹², independent of one another, are H; respectively saturated or unsaturated, branched or unbranched singly or multiply substituted or unsubstituted C₁₋₆ alkyl or C₃₋₆ cycloalkyl; respectively singly or multiply substituted or unsubstituted aryl or heteroaryl; or respectively singly or multiply substituted or unsubstituted aryl bound by saturated or unsaturated C₁₋₃ alkyl or C₁₋₃ alkylene, C₃₋₆ cycloalkyl or heteroaryl; and/or

[0126] R¹³, R¹⁵ and R¹⁷, independent of one another, are H, F, Cl, Br, I, OR¹⁸, SR¹⁸, SO₂R¹⁸, SO₂OR¹⁸, CN, COOR¹⁸, NR¹⁹R²⁰; saturated or unsaturated, branched or unbranched, singly or multiply substituted or unsubstituted C₁₋₆ alkyl, C₃₋₆ cycloalkyl or silyl; singly or multiply substituted or unsubstituted aryl or heteroaryl; respectively singly or multiply substituted or unsubstituted aryl bound by saturated or unsaturated C₁₋₃ alkyl or C₁₋₃ alkylene or ethinyl, C₃₋₆ cycloalkyl or heteroaryl; and/or

[0127] R¹⁴ and R¹⁶, independent of one another, are H, F, Cl, Br, I, SO₂R¹⁸, SO₂OR¹⁸, CN, COOR¹⁸, NR¹⁹R²⁰; saturated or unsaturated, branched or unbranched, singly or multiply substituted or unsubstituted C₁₋₆ alkyl, C₃₋₆ cycloalkyl or silyl; respectively singly or multiply substituted or unsubstituted aryl or heteroaryl; respectively singly or multiply substituted or unsubstituted aryl bound by saturated or unsaturated C₁₋₃ alkyl or C₁₋₃ alkylene or ethinyl, C₃₋₆ cycloalkyl or heteroaryl;

[0128] or the radicals R¹³ and R¹⁴ or R¹⁴ and R¹⁵ together respectively form the group OCH₂O, OCH₂CH₂O, CH═CHO, CH═C(CH₃)O or CH═CHNH and R¹⁵—R¹⁷ or R¹³, R¹⁶ and R¹⁷ have the meaning given above, and/or

[0129] R¹⁸ is respectively saturated or unsaturated, branched or unbranched, unsubstituted or singly or multiply substituted C₁₋₆ alkyl or C₃₋₆ cycloalkyl; unsubstituted or singly or multiply substituted aryl or heteroaryl; or respectively unsubstituted or singly or multiply substituted aryl bound by saturated or unsaturated C₁₋₃ alkyl or C₁₋₃ alkylene or ethinyl, C₃₋₆ cycloalkyl or heteroaryl; and/or

[0130] R¹⁹ and R²⁰, independent of one another, are H; respectively saturated or unsaturated, branched or unbranched, unsubstituted or singly or multiply substituted C₁₋₆ alkyl or C₃₋₆ cycloalkyl; unsubstituted or singly or multiply substituted aryl or heteroaryl; or respectively unsubstituted or singly or multiply substituted aryl bound by saturated or unsaturated C₁₋₃ alkyl or C₁₋₃ alkylene, C₃₋₆ cycloalkyl or heteroaryl;

[0131] or R¹⁹ and R²⁰ together form CH₂CH₂OCH₂CH₂, CH₂CH₂NR¹⁰CH₂CH₂ or (CH₂)₃₋₆, and/or

[0132] R²¹ is H, saturated or unsaturated, branched or unbranched, unsubstituted or singly or multiply substituted C₁₋₆ alkyl.

[0133] C-cyclohexylmethylamine derivatives substituted according to the invention are also particularly preferred in which A is Hydrogen or phenyl, unsubstituted or singly or multiply substituted; preferably hydrogen.

[0134] Substituted C-cyclohexylmethylamine derivatives according to the invention are also preferred, in which

[0135] R² and R3 are saturated or unsaturated, branched or unbranched, unsubstituted or singly or multiply substituted C₁₋₆ alkyl, preferably CH₃, in particular both are CH₃, or R² and R³ together represent CH₂CH₂NR¹⁰CH₂CH₂ or (CH₂)₃₋₆, wherein R⁶ is H or saturated, branched or unbranched, and unsubstituted C₁₋₆ alkyl; in particular H or CH₃.

[0136] Substituted C-cyclohexylmethylamine derivatives according to the invention are a preferred embodiment of the invention, in which

[0137] R¹ is saturated or unsaturated, branched or unbranched C₁₋₆ alkyl; C₃₋₆ cycloalkyl, naphthyl, phenyl, furyl, thiophenyl, naphthyl bound by C₁₋₃ alkylene or ethinyl, phenyl, C₃₋₆ cycloalkyl or thiophenyl bound by C₁₋₃ alkyl or C₁₋₃ alkylene or ethinyl or furyl, which can be unsubstituted or singly or multiply unsubstituted.

[0138] Substituted C-cyclohexylmethylamine derivatives according to the invention are also preferred, in which

[0139] The invention particularly preferably relates to substituted C-cyclohexylmethylamine derivatives of formula I,

[0140] wherein

[0141] A is H; respectively singly or multiply substituted or unsubstituted aryl or heteroaryl;

[0142] R¹ is naphthyl or naphthyl bound by saturated or unsaturated C₁₋₃ alkyl or C₁₋₃ alkylene or ethinyl, respectively unsubstituted or singly or multiply substituted by radicals selected independently of one another from the group consisting of F, Cl, Br, I, OR¹⁸, SR¹⁸, SO₂R¹⁸, SO₂OR¹⁸, CN, COOR¹⁸, and NR¹⁹R²⁰; unsubstituted or singly or multiply substituted C₁₋₁₀ alkyl, C₃₋₁₀ cycloalkyl or silyl; unsubstituted or singly or multiply substituted aryl or heteroaryl; or respectively unsubstituted or singly or multiply substituted aryl bound by saturated or unsaturated C₁₋₃ alkyl or C₁₋₃ alkylene, C₃₋₁₀ cycloalkyl or heteroaryl;

[0143] wherein R¹⁸ is H; respectively saturated or unsaturated, branched or unbranched, unsubstituted or singly or multiply substituted C₁₋₁₀ alkyl or C₃₋₁₀ cycloalkyl; unsubstituted or singly or multiply substituted aryl or heteroaryl; or respectively unsubstituted or singly or multiply substituted aryl bound by saturated or unsaturated C₁₋₃ alkyl or C₁₋₃ alkylene, C₃₋₁₀ cycloalkyl or heteroaryl;

[0144] R¹⁹ and R²⁰, independent of one another, are H; saturated or unsaturated, branched or unbranched, unsubstituted or singly or multiply substituted C₁₋₁₀ alkyl or C₃₋₁₀ cycloalkyl; unsubstituted or singly or multiply substituted aryl or heteroaryl; or respectively unsubstituted or singly or multiply substituted aryl bound by saturated or unsaturated C₁₋₃ alkyl or C₁₋₃ alkylene, C₃₋₁₀ cycloalkyl or heteroaryl;

[0145] or R¹⁹ and R²⁰ together form CH₂CH₂OCH₂CH₂, CH₂CH₂NR²¹CH₂CH₂ or (CH₂)₃₋₆,

[0146] wherein R²¹ is H; saturated or unsaturated, branched or unbranched, unsubstituted or singly or multiply substituted C₁₋₁₀ alkyl;

[0147] R² and R³, independent of one another, are H; respectively saturated or unsaturated, branched or unbranched singly or multiply substituted or unsubstituted C₁₋₁₀ alkyl or C₃₋₁₀ cycloalkyl; respectively singly or multiply substituted or unsubstituted aryl or heteroaryl; or respectively singly or multiply substituted or unsubstituted aryl bound by saturated or unsaturated C₁₋₃ alkyl or C₁₋₃ alkylene, C₃₋₁₀ cycloalkyl or heteroaryl;

[0148] or R² and R³ together represent CH₂CH₂OCH₂CH₂, CH₂CH₂NR⁶CH₂CH₂ or (CH₂)₃₋₆,

[0149] wherein R⁶ is H; respectively saturated or unsaturated, branched or unbranched singly or multiply substituted or unsubstituted C₁₋₁₀ alkyl or C₃₋₁₀ cycloalkyl; respectively singly or multiply substituted or unsubstituted aryl or heteroaryl; or respectively singly or multiply substituted or unsubstituted aryl bound by saturated or unsaturated C₁₋₃ alkyl or C₁₋₃ alkylene, C₃₋₁₀ cycloalkyl or heteroaryl;

[0150] partial formula Ia is:

[0151] wherein B is OH, OR⁷, H, F, Cl or NR⁸R⁹,

[0152] wherein R⁷ is respectively saturated or unsaturated, branched or unbranched singly or multiply substituted or unsubstituted C₁₋₁₀ alkyl or C₃₋₁₀ cycloalkyl; respectively singly or multiply substituted or unsubstituted aryl or heteroaryl; or respectively singly or multiply substituted or unsubstituted aryl bound by saturated or unsaturated C₁₋₃ alkyl or C₁₋₃ alkylene, C₃₋₁₀ cycloalkyl or heteroaryl;

[0153] R⁸ and R⁹, independent of one another, are H; respectively saturated or unsaturated, branched or unbranched singly or multiply substituted or unsubstituted C₁₋₁₀ alkyl or C₃₋₁₀ cycloalkyl; respectively singly or multiply substituted or unsubstituted aryl or heteroaryl; or respectively singly or multiply substituted or unsubstituted aryl bound by saturated or unsaturated C₁₋₃ alkyl or C₁₋₃ alkylene, C₃₋₁₀ cycloalkyl or heteroaryl;

[0154] or R⁸ and R⁹ together form CH₂CH₂OCH₂CH₂, CH₂CH₂NR¹⁰CH₂CH₂ or (CH₂)₃₋₆,

[0155]  wherein R¹⁰ is H; respectively saturated or unsaturated, branched or unbranched singly or multiply substituted or unsubstituted C₁₋₁₀ alkyl or C₃₋₁₀ cycloalkyl; respectively singly or multiply substituted or unsubstituted aryl or heteroaryl; or respectively singly or multiply substituted or unsubstituted aryl bound by saturated or unsaturated C₁₋₃ alkyl or C₁₋₃ alkylene, C₃₋₁₀ cycloalkyl or heteroaryl;

[0156] wherein V is OR⁴,

[0157] wherein R⁴ is COR⁵; respectively saturated or unsaturated, branched or unbranched singly or multiply substituted or unsubstituted C₁₋₁₀ alkyl; saturated or unsaturated, singly or multiply substituted or unsubstituted C₃₋₁₀ cycloalkyl; respectively singly or multiply substituted or unsubstituted aryl or heteroaryl; or respectively singly or multiply substituted or unsubstituted aryl bound by C₁₋₃ alkyl, C₃₋₁₀ cycloalkyl or heteroaryl,

[0158]  wherein R⁵ is saturated or unsaturated, branched or unbranched, singly or multiply substituted or unsubstituted C₁₋₁₀ alkyl; saturated or unsaturated, singly or multiply substituted or unsubstituted C₃₋₁₀ cycloalkyl; respectively singly or multiply substituted or unsubstituted aryl or heteroaryl; or respectively singly or multiply substituted or unsubstituted aryl bound by saturated or unsaturated C₁₋₃ alkyl or C₁₋₃ alkylene, C₃₋₁₀ cycloalkyl or heteroaryl,

[0159] optionally in the form of their racemates, their pure stereoisomers, in particular enantiomers or diastereomers, or in the form of blends of stereoisomers, in particular the enantiomers or diastereomers, in any mixing ratio; in the illustrated form or in the form of their acids or their bases or in the form of their salts, in particular the physiologically acceptable salts, or in the form of their solvates, in particular the hydrates.

[0160] With respect to these particularly preferred substituted C-cyclohexylmethylamine derivatives, in the preferred embodiment

[0161] A is H or respectively singly or multiply substituted or unsubstituted phenyl; preferably H and/or

[0162] R¹ is naphthyl, unsubstituted or singly or multiply substituted by radicals selected independently of one another from the group consisting of

[0163] F, Cl, Br, I, OR¹⁸; and branched or unbranched, unsubstituted or singly or multiply substituted C₁₋₄ alkyl;

[0164] wherein R¹⁸ is H; branched or unbranched, unsubstituted or singly or multiply substituted C₁₋₄ alkyl;

[0165] R¹ is preferably naphthyl, unsubstituted or substituted by OH or OCH₃, and/or

[0166] R² and R³ are saturated or unsaturated, branched or unbranched, unsubstituted or singly or multiply substituted C₁₋₆ alkyl, preferably CH₃, in particular both are CH₃, or R² and R³ together represent CH₂CH₂NR⁶CH₂CH₂ or (CH₂)₄₋₅, in particular together represent CH₂CH₂NR⁶CH₂CH₂, wherein R⁶ is H or saturated, branched or unbranched, and unsubstituted C₁₋₆ alkyl; in particular H or CH₃; and/or

[0167] partial formula Ia is:

[0168] in other words X represents

[0169]  and wherein

[0170] B is OH, OR⁷, H, F, Cl, wherein R⁷ is branched or unbranched, singly or multiply substituted or unsubstituted C₁₋₄ alkyl;

[0171] preferably wherein B is OH, and/or

[0172] wherein V is OR⁴,

[0173] wherein R⁴ is COR⁵; singly or multiply substituted or unsubstituted phenyl or benzyl; in particular COR⁵ or singly or multiply substituted or unsubstituted or benzyl;

[0174] wherein R⁵ is saturated or unsaturated, branched or unbranched, singly or multiply substituted or unsubstituted C₁₋₁₀ alkyl, in particular C₁₋₆ alkyl; or singly or multiply substituted or unsubstituted phenyl.

[0175] Further particularly preferred compounds according to the invention are the group consisting of:

[0176] 4-benzyloxy-1-(4-bromophenyl)-2-dimethylaminomethyl-cyclohexanol;

[0177] 4-benzyloxy-2-dimethylaminomethyl-1-(4-trifluoromethyl-phenyl)-cyclohexanol;

[0178] 4-benzyloxy-1-(3,4-difluorophenyl)-2-dimethylaminomethyl-cyclohexanol;

[0179] 4-benzyloxy-2-dimethylaminomethyl-1-(3-fluoro-4-methyl-phenyl)-cyclohexanol;

[0180] 4-benzyloxy-1-(3,4-dichlorophenyl)-2-dimethylaminomethyl-cyclohexanol;

[0181] 4-benzyloxy-2-dimethylaminomethyl-1-naphthalen-2-yl-cyclohexanol;

[0182] 4-benzyloxy-2-dimethylaminomethyl-1-(3,4-dimethyl-phenyl)-cyclohexanol;

[0183] 4-benzyloxy-2-dimethylaminomethyl-1-(4-fluoro-3-methyl-phenyl)-cyclohexanol; 4-benzyloxy-2-dimethylaminomethyl-1-(5-fluoro-2-methyl-phenyl)-cyclohexanol;

[0184] 4-benzyloxy-1-(3-chloro-4-fluorophenyl)-2-dimethylaminomethyl-cyclohexanol;

[0185] 4-benzyloxy-1-(5-chloro-2-methoxy-phenyl)-2-dimethylaminomethylcyclohexanol;

[0186] 4-benzyloxy-1-(2-bromophenyl)-2-dimethylaminomethyl-cyclohexanol;

[0187] 4-benzyloxy-2-dimethylaminomethyl-1-(2-methoxy-phenyl)-cyclohexanol; 4-benzyloxy-2-dimethylaminomethyl-1-(2-methylsulfanyl-phenyl)-cyclohexanol;

[0188] 4-benzyloxy-1-(4-chlorophenyl)-2-dimethylaminomethyl-cyclohexanol;

[0189] 4-benzyloxy-1-(3-bromophenyl)-2-dimethylaminomethyl-cyclohexanol;

[0190] 4-benzyloxy-1-(4-bromo-3-fluorophenyl)-2-dimethylaminomethyl-cyclohexanol;

[0191] 4-benzyloxy-2-dimethylaminomethyl-1-(4-methoxy-phenyl)-cyclohexanol;

[0192] 4-benzyloxy-1-(2-chlorophenyl)-2-dimethylaminomethyl-cyclohexanol;

[0193] 4-benzyloxy-2-dimethylaminomethyl-1-(3-trifluoromethyl-phenyl)-cyclohexanol;

[0194] 4-benzyloxy-2-dimethylaminomethyl-1-(4-pentyl-phenyl)-cyclohexanol;

[0195] 4-benzyloxy-2-dimethylaminomethyl-1-(2,5-dimethyl-phenyl)-cyclohexanol;

[0196] 4-benzyloxy-2-dimethylaminomethyl-1-(4-isopropyl-phenyl)-cyclohexanol;

[0197] 4-benzyloxy-2-dimethylaminomethyl-1-(2,3-dimethyl-phenyl)-cyclohexanol;

[0198] 4-benzyloxy-2-dimethylaminomethyl-1-(3-fluorophenyl)-cyclohexanol;

[0199] 4-benzyloxy-1-(3,5-bis-trifluoromethyl-phenyl)-2-dimethylaminomethylcyclohexanol;

[0200] 4-benzyloxy-2-dimethylaminomethyl-1-(4-ethyl-phenyl)-cyclohexanol;

[0201] 4-benzyloxy-1-(3,5-dichlorophenyl)-2-dimethylaminomethyl-cyclohexanol;

[0202] 2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-1-o-tolyl-cyclohexanol;

[0203] 2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-1-p-tolyl-cyclohexanol;

[0204] 2-dimethylaminomethyl-1-(2,5-dimethyl-phenyl)-4-(4-fluorobenzyloxy)-cyclohexanol;

[0205] 2-dimethylaminomethyl-1-(3,4-dimethyl-phenyl)-4-(4-fluorobenzyloxy)-cyclohexanol;

[0206] 2-dimethylaminomethyl-1-(3,5-dimethyl-phenyl)-4-(4-fluorobenzyloxy)-cyclohexanol;

[0207] 2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-1-(4-isopropyl-phenyl)-cyclohexanol;

[0208] 2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-1-(3-fluorophenyl)-cyclohexanol;

[0209] 2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-1-(4-fluorophenyl)-cyclohexanol;

[0210] 1-(3,4-difluorophenyl)-2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-cyclohexanol;

[0211] 2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-1-(3-fluoro-4-methyl-phenyl)-cyclohexanol;

[0212] 2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-1-(4-fluoro-3-methyl-phenyl)-cyclohexanol;

[0213] 1-(2-chlorophenyl)-2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-cyclohexanol;

[0214] 1-(3-chlorophenyl)-2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-cyclohexanol;

[0215] 1-(4-chlorophenyl)-2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-cyclohexanol;

[0216] 1-(3,4-dichlorophenyl)-2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-cyclohexanol;

[0217] 1-(4-chloro-3-fluorophenyl)-2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-cyclohexanol;

[0218] 1-(3,5-dichlorophenyl)-2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-cyclohexanol;

[0219] 1-(4-chloro-2-methoxy-phenyl)-2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-cyclohexanol;

[0220] 2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-1-(4-trifluoromethyl-phenyl)-cyclohexanol;

[0221] 1-(3,5-bis-trifluoromethyl-phenyl)-2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-cyclohexanol;

[0222] 2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-1-(2-methoxy-phenyl)-cyclohexanol;

[0223] 2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-1-(2-methylsulfanyl-phenyl)-cyclohexanol;

[0224] (5-benzyloxy-2-thiophen-2-yl-cyclohex-2-enylmethyl)-dimethyl-amine;

[0225] [5-(4-fluorobenzyloxy)-2-thiophen-2-yl-cyclohex-2-enylmethyl]-dimethyl-amine;

[0226] 3,4-dichloro-N-[3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexyl]-benzamide;

[0227] naphthalene-2-carboxylic acid [3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy phenyl)-cyclohexyl]-amide;

[0228] N-[3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexyl]-3-phenyl-propionamide;

[0229] N-[3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexyl]-4-nitro-benzamide;

[0230] N-[3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexyl]-4-methyl-3-nitro-benzamide;

[0231] N-[3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexyl]-3,4,5-trimethoxy-benzamide;

[0232] 2-(4-chlorophenoxy)-N-[3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexyl]-acetamide;

[0233] N-[3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexyl]-3-nitro-benzamide;

[0234] furan-2-carboxylic acid [3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexyl]-amide;

[0235] N-[3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexyl]-2-phenoxy-acetamide;

[0236] N-[3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexyl]-4-trifluoromethyl-benzamide;

[0237] N-[3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexyl]-4-methoxy-benzamide;

[0238] 2-dimethylaminomethyl-1-(4-fluorophenyl)-4-phenethyl-cyclohexanol;

[0239] 1-(4-bromophenyl)-2-dimethylaminomethyl-4-phenethyl-cyclohexanol;

[0240] 2-dimethylaminomethyl-1-(4-ethyl-phenyl)-4-phenethyl-cyclohexanol;

[0241] 2-dimethylaminomethyl-1-(4-isopropyl-phenyl)-4-phenethyl-cyclohexanol;

[0242] 2-dimethylaminomethyl-1-(4-methoxy-phenyl)-4-phenethyl-cyclohexanol;

[0243] 2-dimethylaminomethyl-1-(2,4-dimethyl-phenyl)-4-phenethyl-cyclohexanol;

[0244] 2-dimethylaminomethyl-1-(2-methylsulfanyl-phenyl)-4-phenethyl-cyclohexanol;

[0245] 2-dimethylaminomethyl-1-(5-fluoro-2-methyl-phenyl)-4-phenethyl-cyclohexanol;

[0246] 2-dimethylaminomethyl-1-(2,5-dimethyl-phenyl)-4-phenethyl-cyclohexanol;

[0247] 2-dimethylaminomethyl-4-phenethyl-1-p-tolyl-cyclohexanol;

[0248] 2-dimethylaminomethyl-1-(3-fluorophenyl)-4-phenethyl-cyclohexanol;

[0249] 1-(3-chlorophenyl)-2-dimethylaminomethyl-4-phenethyl-cyclohexanol;

[0250] 1-(4-chloro-3-fluorophenyl)-2-dimethylaminomethyl-4-phenethyl-cyclohexanol;

[0251] 2-dimethylaminomethyl-4-phenethyl-1-(3-trifluoromethyl-phenyl)-cyclohexanol;

[0252] 1-(3,5-dichlorophenyl)-2-dimethylaminomethyl-4-phenethyl-cyclohexanol;

[0253] 2-dimethylaminomethyl-1-(3,4-dimethyl-phenyl)-4-phenethyl-cyclohexanol;

[0254] 1-(3,4-dichlorophenyl)-2-dimethylaminomethyl-4-phenethyl-cyclohexanol;

[0255] 1-(4-chlorophenyl)-2-dimethylaminomethyl-4-phenethyl-cyclohexanol;

[0256] 2-dimethylaminomethyl-1-(3-fluoro-4-methyl-phenyl)-4-phenethyl-cyclohexanol;

[0257] 2-dimethylaminomethyl-1-(3,5-dimethyl-phenyl)-4-phenethyl-cyclohexanol;

[0258] 1-(4-bromo-3-fluorophenyl)-2-dimethylaminomethyl-4-phenethyl-cyclohexanol;

[0259] 1-(3,4-difluorophenyl)-2-dimethylaminomethyl-4-phenethyl-cyclohexanol;

[0260] 2-dimethylaminomethyl-1-(2,3-dimethyl-phenyl)-4-phenethyl-cyclohexanol;

[0261] 2-dimethylaminomethyl-1-naphthalen-1-yl-4-phenethyl-cyclohexanol;

[0262] 1-(3,5-bis-trifluoromethyl-phenyl)-2-dimethylaminomethyl-4-phenethylcyclohexanol;

[0263] 1-(3-bromophenyl)-2-dimethylaminomethyl-4-phenethyl-cyclohexanol;

[0264] 2-dimethylaminomethyl-1-(4-fluoro-3-methyl-phenyl)-4-phenethyl-cyclohexanol;

[0265] 2-dimethylaminomethyl-4-phenethyl-1-m-tolyl-cyclohexanol;

[0266] 4-benzyl-2-dimethylaminomethyl-1-m-tolyl-cyclohexanol;

[0267] 4-benzyl-1-(3,4-difluorophenyl)-2-dimethylaminomethyl-cyclohexanol;

[0268] 4-benzyl-2-dimethylaminomethyl-1-p-tolyl-cyclohexanol;

[0269] 2-dimethylaminomethyl-4-(3-methoxy-benzyl)-1-p-tolyl-cyclohexanol;

[0270] 1-(4-chlorophenyl)-2-dimethylaminomethyl-4-(3-methoxy-benzyl)-cyclohexanol;

[0271] 1-(4-bromo-3-fluorophenyl)-2-dimethylaminomethyl-4-(3-methoxy-benzyl)-cyclohexanol;

[0272] 2-dimethylaminomethyl-4-(4-fluorobenzyl)-1-p-tolyl-cyclohexanol;

[0273] 1-(4-chlorophenyl)-2-dimethylaminomethyl-4-(4-fluorobenzyl)-cyclohexanol;

[0274] dimethyl-[2-(5-methyl-thiophen-2-yl)-5-phenethyl-cyclohex-2-eny[methyl]amine;

[0275] [2-(3,5-bis-trifluoromethyl-phenyl)-5-phenethyl-cyclohex-1-enylmethyl]-dimethylamine;

[0276] dimethyl-(5-phenethyl-2-p-tolyl-cyclohex-1-enylmethyl)-amine;

[0277] [2-(3-chloro-4-fluorophenyl)-5-phenethyl-cyclohex-1-enylmethyl]-dimethyl-amine;

[0278] [2-(2,5-dimethyl-phenyl)-5-phenethyl-cyclohex-1-enylmethyl]-dimethyl-amine;

[0279] dimethyl-(5-phenethyl-2-p-tolyl-cyclohex-2-enylmethyl)-amine;

[0280] [2-(3,5-bis-trifluoromethyl-phenyl)-5-phenethyl-cyclohex-2-enylmethyl]-dimethyl-amine;

[0281] [2-(3-chloro-4-fluorophenyl)-5-phenethyl-cyclohex-2-enylmethyl]-dimethyl-amine;

[0282] [2-(3-chloro-4-fluorophenyl)-2-fluoro-5-phenethyl-cyclohexylmethyl]-dimethylamine;

[0283] [2-fluoro-5-(4-fluorobenzyl)-2-p-tolyl-cyclohexylmethyl]-dimethyl-amine;

[0284] benzyl-2-(dimethylamino-phenyl-methyl)-4-phenyl-cyclohexanol;

[0285] 2-(dimethylamino-phenyl-methyl)-4-phenyl-1-vinyl-cyclohexanol;

[0286] 1-(4-tert-butyl-phenyl)-2-(dimethylamino-phenyl-methyl)-4-phenylcyclohexanol;

[0287] 2-(dimethylamino-phenyl-methyl)-4-phenyl-1-m-tolyl-cyclohexanol;

[0288] 2-(dimethylamino-phenyl-methyl)-1-phenethyl-4-phenyl-cyclohexanol;

[0289] 2-(dimethylamino-phenyl-methyl)-4-phenyl-1-phenylethynyl-cyclohexanol;

[0290] 2-(dimethylamino-phenyl-methyl)-1-(3-methoxy-phenyl)-4-phenyl-cyclohexanol;

[0291] 2-(dimethylamino-phenyl-methyl)-4-phenyl-1-(3-phenyl-propyl)-cyclohexanol;

[0292] 2-(dimethylamino-phenyl-methyl)-1-(4-methoxy-phenyl)-4-phenyl-cyclohexanol;

[0293] 2-(dimethylamino-phenyl-methyl)-1-(2-methoxy-phenyl)-4-phenyl-cyclohexanol;

[0294] 4-benzyloxy-2-dimethylaminomethyl-1-phenyl-cyclohexanol;

[0295] 1-benzyl-4-benzyloxy-2-dimethylaminomethyl-cyclohexanol;

[0296] 4-benzyloxy-2-dimethylaminomethyl-1-(4-fluoro-3-methyl-phenyl)-cyclohexanol;

[0297] 4-benzyloxy-2-dimethylaminomethyl-1-o-tolyl-cyclohexanol;

[0298] 4-benzyloxy-2-dimethylaminomethyl-1-vinyl-cyclohexanol;

[0299] 4-benzyloxy-1-cyclopentyl-2-dimethylaminomethyl-cyclohexanol;

[0300] 4-benzyloxy-2-dimethylaminomethyl-1-m-tolyl-cyclohexanol;

[0301] 4-benzyloxy-2-dimethylaminomethyl-bicyclohexyl-1-ol;

[0302] 4-benzyloxy-2-dimethylaminomethyl-1-(4-fluorophenyl)-cyclohexanol;

[0303] 4-benzyloxy-2-dimethylaminomethyl-1-phenylethynyl-cyclohexanol;

[0304] 4-benzyloxy-2-dimethylaminomethyl-1-thiophen-2-yl-cyclohexanol;

[0305] 4-benzyloxy-2-dimethylaminomethyl-1-(3-methoxy-phenyl)-cyclohexanol;

[0306] 4-benzyloxy-2-dimethylaminomethyl-1-(3-phenyl-propyl)-cyclohexanol;

[0307] 4-benzyloxy-2-dimethylaminomethyl-1-p-tolyl-cyclohexanol;

[0308] 4-benzyloxy-2-dimethylaminomethyl-1-(4-methoxy-phenyl)-cyclohexanol; 4-benzyloxy-2-dimethylaminomethyl-1-(3-fluorophenyl)-cyclohexanol;

[0309] 4-benzyloxy-1-(3-chlorophenyl)-2-dimethylaminomethyl-cyclohexanol;

[0310] 4-benzyloxy-2-dimethylaminomethyl-1-(3-methoxy-benzyl)-cyclohexanol;

[0311] 4-benzyloxy-1-(4-chloro-3-trifluoromethyl-phenyl)-2-dimethylaminomethyl-cyclohexanol;

[0312] 4-benzyloxy-2-dimethylaminomethyl-1-(3-fluorobenzyl)-cyclohexanol;

[0313] 4-benzyloxy-2-dimethylaminomethyl-1-(2-methyl-benzyl)-cyclohexanol;

[0314] 4-benzyloxy-2-dimethylaminomethyl-1-(2,5-dimethyl-benzyl)-cyclohexanol;

[0315] 4-(4-chlorobenzyl)-2-dimethylaminomethyl-1-(3-methoxy-phenyl)-cyclohexanol;

[0316] 4-(4-chlorobenzyl)-2-dimethylaminomethyl-1-(3-phenyl-propyl)-cyclohexanol;

[0317] 4-(4-chlorobenzyl)-1-(2,3-dichlorophenyl)-2-dimethylaminomethyl-cyclohexanol;

[0318] 4-(4-chlorobenzyl)-1-cyclohexylmethyl-2-dimethylaminomethyl-cyclohexanol;

[0319] 4-(4-chlorobenzyl)-2-dimethylaminomethyl-1-(5-fluoro-2-methoxy-phenyl)-cyclohexanol;

[0320] 4-(4-chlorobenzyl)-2-dimethylaminomethyl-1-(3-fluorophenyl)-cyclohexanol;

[0321] 4-(4-chlorobenzyl)-1-(3-chlorophenyl)-2-dimethylaminomethyl-cyclohexanol;

[0322] 4-(4-chlorobenzyl)-1-(3,5-dichlorophenyl)-2-dimethylaminomethyl-cyclohexanol;

[0323] 4-(4-chlorobenzyl)-1-(2-chlorobenzyl)-2-dimethylaminomethyl-cyclohexanol;

[0324] 4-(4-chlorobenzyl)-2-dimethylaminomethyl-1-(4-fluorobenzyl)-cyclohexanol;

[0325] 4-(4-chlorobenzyl)-2-dimethylaminomethyl-1-(3-fluorobenzyl)-cyclohexanol;

[0326] 4-(4-chlorobenzyl)-2-dimethylaminomethyl-1-(2-methoxy-phenyl)-cyclohexanol;

[0327] 4-(4-chlorobenzyl)-2-dimethylaminomethyl-1-(2-methyl-benzyl)-cyclohexanol;

[0328] 4-(4-chlorobenzyl)-2-dimethylaminomethyl-1-(3-methyl-benzyl)-cyclohexanol;

[0329] 1,4-bis-(4-chlorobenzyl)-2-dimethylaminomethyl-cyclohexanol;

[0330] 4-(4-chlorobenzyl)-1-(2-chloro-6-fluorobenzyl)-2-dimethylaminomethyl-cyclohexanol;

[0331] 4-(4-chlorobenzyl)-2-dimethylaminomethyl-1-(2,5-dimethyl-benzyl)-cyclohexanol;

[0332] 4-(4-chlorobenzyl)-1-(3-chlorobenzyl)-2-dimethylaminomethyl-cyclohexanol;

[0333] 4-(4-chlorobenzyl)-1-(2,4-dichlorobenzyl)-2-dimethylaminomethyl-cyclohexanol;

[0334] 4-(4-chlorobenzyl)-2-dimethylaminomethyl-1-phenyl-cyclohexanol;

[0335] 4-(4-chlorobenzyl)-1-(4-chlorophenyl)-2-dimethylaminomethyl-cyclohexanol;

[0336] 4-(4-chlorobenzyl)-2-dimethylaminomethyl-1-(4-fluoro-3-methyl-phenyl)-cyclohexanol;

[0337] 4-(4-chlorobenzyl)-2-dimethylaminomethyl-1-o-tolyl-cyclohexanol;

[0338] 4-(4-chlorobenzyl)-2-dimethylaminomethyl-1-vinyl-cyclohexanol;

[0339] 4-(4-chlorobenzyl)-1-cyclopentyl-2-dimethylaminomethyl-cyclohexanol;

[0340] 4-(4-chlorobenzyl)-2-dimethylaminomethyl-1-m-tolyl-cyclohexanol;

[0341] 4-(4-chlorobenzyl)-2-dimethylaminomethyl-bicyclohexyl-1-ol;

[0342] 4-(4-chlorobenzyl)-2-dimethylaminomethyl-1-(4-fluorophenyl)-cyclohexanol;

[0343] 4-(4-chlorobenzyl)-2-dimethylaminomethyl-1-phenethyl-cyclohexanol;

[0344] 4-(4-chlorobenzyl)-2-dimethylaminomethyl-1-phenylethynyl-cyclohexanol;

[0345] 4-(4-chlorobenzyl)-2-dimethylaminomethyl-1-thiophen-2-yl-cyclohexanol;

[0346] 4-(4-chlorobenzyl)-2-dimethylaminomethyl-1-p-tolyl-cyclohexanol;

[0347] 4-(4-chlorobenzyl)-2-dimethylaminomethyl-1-(4-methoxy-phenyl)-cyclohexanol;

[0348] 4-(4-chlorobenzyl)-2-dimethylaminomethyl-1-trimethylsilanylethynyl-cyclohexanol;

[0349] 4-(4-chlorobenzyl)-1-(4-chloro-3-trifluoromethyl-phenyl)-2-dimethylaminomethyl-cyclohexanol;

[0350] 4-(4-chlorobenzyl)-1-(3-chloro-4-fluorophenyl)-2-dimethylaminomethyl-cyclohexanol;

[0351] 4-(4-chlorobenzyl)-2-dimethylaminomethyl-1-(3-trifluoromethyl-phenyl)-cyclohexanol;

[0352] 2-dimethylaminomethyl-4-(4-fluorobenzyl)-1-phenyl-cyclohexanol; 0.1-(4-chlorophenyl)-2-dimethylaminomethyl-4-(4-fluorobenzyl)-cyclohexanol; 1-benzyl-2-dimethylaminomethyl-4-(4-fluorobenzyl)-cyclohexanol;

[0353] 2-dimethylaminomethyl-4-(4-fluorobenzyl)-1-(4-fluoro-3-methyl-phenyl)-cyclohexanol;

[0354] 2-dimethylaminomethyl-4-(4-fluorobenzyl)-1-o-tolyl-cyclohexanol;

[0355] 2-dimethylaminomethyl-4-(4-fluorobenzyl)-1-vinyl-cyclohexanol;

[0356] 1-(4-tert-butyl-phenyl)-2-dimethylaminomethyl-4-(4-fluorobenzyl)-cyclohexanol;

[0357] 1-cyclopentyl-2-dimethylaminomethyl-4-(4-fluorobenzyl)-cyclohexanol;

[0358] 2-dimethylaminomethyl-4-(4-fluorobenzyl)-1-m-tolyl-cyclohexanol;

[0359] 2-dimethylaminomethyl-4-(4-fluorobenzyl)-bicyclohexyl-1-ol;

[0360] 2-dimethylaminomethyl-4-(4-fluorobenzyl)-1-(4-fluorophenyl)-cyclohexanol;

[0361] 2-dimethylaminomethyl-4-(4-fluorobenzyl)-1-phenethyl-cyclohexanol;

[0362] 2-dimethylaminomethyl-4-(4-fluorobenzyl)-1-phenylethynyl-cyclohexanol;

[0363] 2-dimethylaminomethyl-4-(4-fluorobenzyl)-1-thiophen-2-yl-cyclohexanol;

[0364] 2-dimethylaminomethyl-4-(4-fluorobenzyl)-1-(3-methoxy-phenyl)-cyclohexanol;

[0365] 2-dimethylaminomethyl-4-(4-fluorobenzyl)-1-(3-phenyl-propyl)-cyclohexanol;

[0366] 1-(2,3-dichlorophenyl)-2-dimethylaminomethyl-4-(4-fluorobenzyl)-cyclohexanol;

[0367] 2-dimethylaminomethyl-4-(4-fluorobenzyl)-1-p-tolyl-cyclohexanol;

[0368] 2-dimethylaminomethyl-4-(4-fluorobenzyl)-1-(4-methoxy-phenyl)-cyclohexanol; 1-cyclohexylmethyl-2-dimethylaminomethyl-4-(4-fluorobenzyl)-cyclohexanol;

[0369] 2-dimethylaminomethyl-4-(4-fluorobenzyl)-1-(5-fluoro2-methoxy-phenyl)-cyclohexanol;

[0370] 2-dimethylaminomethyl-4-(4-fluorobenzyl)-1-(3-fluorophenyl)-cyclohexanol;

[0371] 1-(3-chlorophenyl)-2-dimethylaminomethyl-4-(4-fluorobenzyl)-cyclohexanol;

[0372] 1-(3,5-dichlorophenyl)-2-dimethylaminomethyl-4-(4-fluorobenzyl)-cyclohexanol;

[0373] 1-(2-chlorobenzyl)-2-dimethylaminomethyl-4-(4-fluorobenzyl)-cyclohexanol;

[0374] 2-dimethylaminomethyl-1,4-bis-(4-fluorobenzyl)-cyclohexanol;

[0375] 2-dimethylaminomethyl-4-(4-fluorobenzyl)-1-(3-methoxy-benzyl)-cyclohexanol;

[0376] 1-(4-chloro-3-trifluoromethyl-phenyl)-2-dimethylaminomethyl-4-(4-fluorobenzyl)-cyclohexanol;

[0377] 2-dimethylaminomethyl-4-(4-fluorobenzyl)-1-(3-fluorobenzyl)-cyclohexanol;

[0378] 2-dimethylaminomethyl-4-(4-fluorobenzyl)-1-(2-methoxy-phenyl)-cyclohexanol;

[0379] 2-dimethylaminomethyl-4-(4-fluorobenzyl)-1-(2-methyl-benzyl)-cyclohexanol;

[0380] 1-(3-chloro-4-fluorophenyl)-2-dimethylaminomethyl-4-(4-fluorobenzyl)-cyclohexanol;

[0381] 2-dimethylaminomethyl-4-(4-fluorobenzyl)-1-(3-trifluoromethyl-phenyl)-cyclohexanol;

[0382] 2-dimethylaminomethyl-4-(4-fluorobenzyl)-1-(3-methyl-benzyl)-cyclohexanol;

[0383] 1-(4-chlorobenzyl)-2-dimethylaminomethyl-4-(4-fluorobenzyl)-cyclohexanol;

[0384] 1-(2-chloro-6-fluorobenzyl)-2-dimethylaminomethyl-4-(4-fluorobenzyl)-cyclohexanol;

[0385] 2-dimethylaminomethyl-1-(2,5-dimethyl-benzyl)-4-(4-fluorobenzyl)-cyclohexanol;

[0386] 1-(3-chlorobenzyl)-2-dimethylaminomethyl-4-(4-fluorobenzyl)-cyclohexanol;

[0387] 1-(2,4-dichlorobenzyl)-2-dimethylaminomethyl-4-(4-fluorobenzyl)-cyclohexanol;

[0388] 2-dimethylaminomethyl-4-(3-methoxy-benzyl)-1-phenyl-cyclohexanol;

[0389] 1-benzyl-2-dimethylaminomethyl-4-(3-methoxy-benzyl)-cyclohexanol;

[0390] 2-dimethylaminomethyl-1-(4-fluoro-3-methyl-phenyl)-4-(3-methoxy-benzyl)-cyclohexanol;

[0391] 2-dimethylaminomethyl-4-(3-methoxy-benzyl)-1-o-tolyl-cyclohexanol;

[0392] 2-dimethylaminomethyl-4-(3-methoxy-benzyl)-1-vinyl-cyclohexanol;

[0393] 1-(4-tert-butyl-phenyl)-2-dimethylaminomethyl-4-(3-methoxy-benzyl)-cyclohexanol;

[0394] 1-cyclopentyl-2-dimethylaminomethyl-4-(3-methoxy-benzyl)-cyclohexanol;

[0395] 2-dimethylaminomethyl-4-(3-methoxy-benzyl)-1-m-tolyl-cyclohexanol;

[0396] 2-dimethylaminomethyl-4-(3-methoxy-benzyl)-bicyclohexyl-1-ol;

[0397] 2-dimethylaminomethyl-4-(3-methoxy-benzyl)-1-phenethyl-cyclohexanol;

[0398] 2-dimethylaminomethyl-4-(3-methoxy-benzyl)-1-phenylethynyl-cyclohexanol

[0399] 2-dimethylaminomethyl-4-(3-methoxy-benzyl)-1-thiophen-2-yl-cyclohexanol;

[0400] 2-dimethylaminomethyl-4-(3-methoxy-benzyl)-1-(3-methoxy-phenyl)-cyclohexanol;

[0401] 2-dimethylaminomethyl-4-(3-methoxy-benzyl)-1-(3-phenyl-propyl)-cyclohexanol;

[0402] 1-(2,3-dichlorophenyl)-2-dimethylaminomethyl-4-(3-methoxy-benzyl)-cyclohexanol;

[0403] 2-dimethylaminomethyl-4-(3-methoxy-benzyl)-1-p-tolyl-cyclohexanol;

[0404] 1-cyclohexylmethyl-2-dimethylaminomethyl-4-(3-methoxy-benzyl)-cyclohexanol;

[0405] 2-dimethylaminomethyl-1-(5-fluoro-2-methoxy-phenyl)-4-(3-methoxy-benzyl)—cyclohexanol;

[0406] 1-(3-chlorophenyl)-2-dimethylaminomethyl-4-(3-methoxy-benzyl)-cyclohexanol;

[0407] 1-(3,5-dichlorophenyl)-2-dimethylaminomethyl-4-(3-methoxy-benzyl)-cyclohexanol;

[0408] 1-(4-chloro-3-trifluoromethyl-phenyl)-2-dimethylaminomethyl-4-(3-methoxybenzyl)-cyclohexanol;

[0409] 2-dimethylaminomethyl-1-(3-fluorobenzyl)-4-(3-methoxy-benzyl)-cyclohexanol;

[0410] 2-dimethylaminomethyl-4-(3-methoxy-benzyl)-1-(2-methoxy-phenyl)-cyclohexanol;

[0411] 2-dimethylaminomethyl-4-(3-methoxy-benzyl)-1-(3-trifluoromethyl-phenyl)-cyclohexanol;

[0412] 1 (2-chloro-6-fluorobenzyl)-2-dimethylaminomethyl-4-(3-methoxy-benzyl)-cyclohexanol;

[0413] 2-dimethylaminomethyl-1-(2,5-dimethyl-benzyl)-4-(3-methoxy-benzyl)-cyclohexanol;

[0414] 1-(3-chlorobenzyl)-2-dimethylaminomethyl-4-(3-methoxy-benzyl)-cyclohexanol;

[0415] 2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-1-phenyl-cyclohexanol;

[0416] 1-benzyl-2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-cyclohexanol;

[0417] 2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-1-(4-fluoro-3-methyl-phenyl)-cyclohexanol;

[0418] 2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-1-vinyl-cyclohexanol;

[0419] 1-(4-tert-butyl-phenyl)-2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-cyclohexanol;

[0420] 1-cyclopentyl-2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-cyclohexanol;

[0421] 2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-1-m-tolyl-cyclohexanol;

[0422] 2-dimethylaminomethyl-4-(4-fluorobenzyloxy)bicyclohexyl-1-ol;

[0423] 2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-1-phenethyl-cyclohexanol;

[0424] 2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-1-phenylethynyl-cyclohexanol;

[0425] 2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-1-thiophen-2-yl-cyclohexanol;

[0426] 2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-1-(3-methoxy-phenyl)-cyclohexanol;

[0427] 2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-1-p-tolyl-cyclohexanol; 1-cyclohexylmethyl-2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-cyclohexanol;

[0428] 2-dimethylaminomethyl-1-(3-fluorobenzyl)-4-(4-fluorobenzyloxy)-cyclohexanol;

[0429] 2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-1-(2-methoxy-phenyl)-cyclohexanol;

[0430] 2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-1-(3-methyl-benzyl)-cyclohexanol;

[0431] 2-dimethylaminomethyl-1-(2,5-dimethyl-benzyl)-4-(4-fluorobenzyloxy)-cyclohexanol;

[0432] 1-(3-chlorobenzyl)-2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-cyclohexanol;

[0433] [5-benzyloxy-2-(3-methoxy-phenyl)-cyclohexylmethyl]-dimethyl-amine;

[0434] [5-(3-chlorobenzyloxy)-2-(3-methoxy-phenyl)-cyclohexylmethyl]-dimethyl-amine;

[0435] [2-(3-methoxy-phenyl)-5-(naphthalen-2-ylmethoxy)-cyclohexylmethyl]-dimethylamine;

[0436] [5-(3-methoxy-benzyloxy)-2-(3-methoxy-phenyl)-cyclohexylmethyl]-dimethylamine;

[0437] [5-(4-chlorobenzyloxy)-2-(3-methoxy-phenyl)-cyclohexylmethyl]-dimethyl-amine;

[0438] [5-(4-methoxy-benzyloxy)-2-(3-methoxy-phenyl)-cyclohexylmethyl]-dimethylamine;

[0439] 2-dimethylaminomethyl-1-(3-methoxy-phenyl)-4-(naphthalen-2-ylmethoxy)-cyclohexanol;

[0440] [5-(4-methoxy-benzyloxy)-2-(3-methoxy-phenyl)-cyclohex-2-enylmethyl]dimethyl-amine;

[0441] butyric acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexylester;

[0442] 4-amino-2-dimethylaminomethyl-1-(3-methoxy-phenyl)-cyclohexanol;

[0443] 2-dimethylaminomethyl-1-(3-methoxy-phenyl)-4-(naphthalen-2-ylmethoxy)-cyclohexanol;

[0444] 4-methoxy-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxyphenyl)-cyclohexylester;

[0445] 3-methoxy-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxyphenyl)-cyclohexylester;

[0446] 2,2-dimethyl-propionic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxyphenyl)-cyclohexylester;

[0447] butyric acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexylester;

[0448] 4-methoxy-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxyphenyl)-cyclohexylester;

[0449] 3-methoxy-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxyphenyl)-cyclohexylester;

[0450] 2,2-dimethyl-propionic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxyphenyl)-cyclohexylester;

[0451] 3,4-dimethoxy-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxyphenyl)-cyclohexylester;

[0452] 3,4-dimethoxy-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxyphenyl)-cyclohexylester;

[0453] naphthalene-2-carboxylic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexylester;

[0454] 4-methyl-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxyphenyl)-cyclohexylester;

[0455] 3,4-dichloro-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxyphenyl)-cyclohexylester;

[0456] 4-chloro-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxyphenyl)-cyclohexylester;

[0457] 3-chloro-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxyphenyl)-cyclohexylester;

[0458] 2-chloro-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxyphenyl)-cyclohexylester;

[0459] 4-trifluoromethyl-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3methoxy-phenyl)-cyclohexylester;

[0460] 3,5-difluoro-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexylester;

[0461] 4-fluoro-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexylester;

[0462] 3-fluoro-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexylester;

[0463] 2-fluoro-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexylester;

[0464] cyclopentanecarboxylic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxyphenyl)-cyclohexylester;

[0465] (4-methoxy-phenyl)-acetic acid 3-dimethylaminomethyl-4-hydroxy-4-(3methoxy-phenyl)-cyclohexylester;

[0466] (3-methoxy-phenyl)-acetic acid 3-dimethylaminomethyl-4-hydroxy-4-(3methoxy-phenyl)-cyclohexylester;

[0467] phenyl-acetic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexylester;

[0468] 3,4,5-trimethoxy-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3methoxy-phenyl)-cyclohexylester;

[0469] 3,5-dimethoxy-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxyphenyl)-cyclohexylester;

[0470] naphthalene-1-carboxylic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxyphenyl)-cyclohexylester;

[0471] 2-methoxy-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxyphenyl)-cyclohexylester;

[0472] naphthalene-2-carboxylic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxyphenyl)-cyclohexylester;

[0473] 2-hydroxy-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxyphenyl)-cyclohexylester;

[0474] 4-methyl-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxyphenyl)-cyclohexylester;

[0475] 3,4-dichloro-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexylester;

[0476] 4-chloro-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxyphenyl)-cyclohexylester;

[0477] 3-chloro-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxyphenyl)-cyclohexylester;

[0478] 2-chloro-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxyphenyl)-cyclohexylester;

[0479] 4-trifluoromethyl-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexylester;

[0480] 3,5-difluoro-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexylester;

[0481] 4-fluoro-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexylester;

[0482] 3-fluoro-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexylester;

[0483] 2-fluoro-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexylester;

[0484] cyclopentanecarboxylic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexylester;

[0485] (4-methoxy-phenyl)-acetic acid 3-dimethylaminomethyl-4-hydroxy-3234-(3-methoxy-phenyl)-cyclohexylester;

[0486] (3-methoxy-phenyl)-acetic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexylester;

[0487] phenyl-acetic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexylester;

[0488] 3,4,5-trimethoxy-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexylester;

[0489] 3,5-dimethoxy-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxyphenyl)-cyclohexylester;

[0490] naphthalene-1-carboxylic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexylester;

[0491] 2-methoxy-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxyphenyl)-cyclohexylester;

[0492] 2-dimethylaminomethyl-1,4-bis-(3-methoxy-phenyl)-cyclohexane-1,4-diol;

[0493] 2-dimethylaminomethyl-1,4-bis-(3-methoxy-phenyl)-cyclohexane-1,4-diol;

[0494] 6-(4-benzyloxy-2-dimethylaminomethyl-1-hydroxy-cyclohexyl)-naphthalen-2-ol;

[0495] 4-benzyloxy-2-dimethylaminomethyl-1-(6-methoxy-naphthalen-2-yl)-cyclohexanol;

[0496] butyric acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexylester;

[0497] butyric acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexylester;

[0498] 2-dimethylaminomethyl-1-(3-methoxy-phenyl)-4-methylamino-cyclohexanol;

[0499] 2-dimethylaminomethyl-1-(3-methoxy-phenyl-4-methylamino-cyclohexanol;

[0500] valeric acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexylester;

[0501] [3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexylidene] acetic acid ethylester;

[0502] [3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexylidene] acetic acid ethylester;

[0503] 3-[2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-1-hydroxy-cyclohexyl]-phenol;

[0504] 4-benzyloxy-2-dimethylaminomethyl-1-(3-phenyl-propyl)-cyclohexanol;

[0505] 2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-1-(3-phenyl-propyl)-cyclohexanol;

[0506] 2-dimethylaminomethyl-1-(3-fluorobenzyl)-4-(4-fluorobenzyloxy)-cyclohexanol;

[0507] 4-benzyloxy-2-dimethylaminomethyl-1-(3-fluorobenzyl)-cyclohexanol;

[0508] 2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-1-p-tolyl-cyclohexanol;

[0509] 4-benzyloxy-2-dimethylaminomethyl-1-p-tolyl-cyclohexanol;

[0510] 2-dimethylaminomethyl-1-(2,5-dimethyl-benzyl)-4-(4-fluorobenzyloxy)-cyclohexanol;

[0511] 4-benzyloxy-2-dimethylaminomethyl-1-(2,5-dimethyl-benzyl)-cyclohexanol;

[0512] 1-(4-chloro-3-trifluoromethyl-phenyl)-2-dimethylaminomethyl-4-(4-fluorbenzyloxy)-cyclohexanol;

[0513] 4-benzyloxy-1-(4-chloro-3-trifluoromethyl-phenyl)-2-dimethylaminomethyl-cyclohexanol;

[0514] [2,5-bis-(4-fluorobenzyloxy)-2-(3-methoxy-phenyl)-cyclohexylmethyl]-dimethylamine;

[0515] 5-dimethylaminomethyl-4-(3-methoxy-phenyl)-cyclohex-3-enol;

[0516] 2-dimethylaminomethyl-1-(6-methoxynaphthalen-2-yl)-cyclohexane-1,4-diol;

[0517] butyric acid 3-dimethylaminomethyl-4-hydroxy-4-(6-methoxynaphthalen-2-yl)-cyclohexylester;

[0518] benzoic acid 4-hydroxy-3-(4-methyl-piperazin-1-ylmethyl)-4-naphthalen-2-yl-cyclohexyl ester;

[0519] 2-chloro-benzoic acid 4-hydroxy-3-(4-methyl-piperazin-1-ylmethyl)-4naphthalen-2-yl-cyclohexyl ester;

[0520] 3-chloro-benzoic acid 4-hydroxy-3-(4-methyl-piperazin-1-ylmethyl)-4naphthalen-2-yl-cyclohexyl ester;

[0521] 4-chloro-benzoic acid 4-hydroxy-3-(4-methyl-piperazin-1-ylmethyl)-4naphthalen-2-yl-cyclohexyl ester;

[0522] 2-fluoro-benzoic acid 4-hydroxy-3-(4-methyl-piperazin-1-ylmethyl)-4naphthalen-2-yl-cyclohexyl ester;

[0523] 3-fluoro-benzoic acid 4-hydroxy-3-(4-methyl-piperazin-1-ylmethyl)-4naphthalen-2-yl-cyclohexyl ester;

[0524] 4-fluoro-benzoic acid 4-hydroxy-3-(4-methyl-piperazin-1-ylmethyl)-4naphthalen-2-yl-cyclohexyl ester;

[0525] 2-methyl-benzoic acid 4-hydroxy-3-(4-methyl-piperazin-1-ylmethyl)-4naphthalen-2-yl-cyclohexyl ester;

[0526] 3-methyl-benzoic acid 4-hydroxy-3-(4-methyl-piperazin-1-ylmethyl)-4naphthalen-2-yl-cyclohexyl ester;

[0527] 4-methyl-benzoic acid 4-hydroxy-3-(4-methyl-piperazin-1-ylmethyl)-4naphthalen-2-yl-cyclohexyl ester;

[0528] 2-methoxy-benzoic acid 4-hydroxy-3-(4-methyl-piperazin-1-ylmethyl)-4naphthalen-2-yl-cyclohexyl ester;

[0529] 3-methoxy-benzoic acid 4-hydroxy-3-(4-methyl-piperazin-1-ylmethyl)-4naphthalen-2-yl-cyclohexyl ester;

[0530] 4-methoxy-benzoic acid 4-hydroxy-3-(4-methyl-piperazin-1-ylmethyl)-4naphthalen-2-yl-cyclohexyl ester;

[0531] 2,6-dichloro-benzoic acid 4-hydroxy-3-(4-methyl-piperazin-1-ylmethyl)-4naphthalen-2-yl-cyclohexyl ester;

[0532] 2,6-difluoro-benzoic acid 4-hydroxy-3-(4-methyl-piperazin-1-ylmethyl)-4naphthalen-2-yl-cyclohexyl ester;

[0533] 2-chloro5-fluoro-benzoic acid 4-hydroxy-3-(4-methyl-piperazin-1-ylmethyl)-4-naphthalen-2-yl-cyclohexyl ester;

[0534] biphenyl-4-carboxylic acid 4-hydroxy-3-(4-methyl-piperazin-1-ylmethyl)-4naphthalen-2-yl-cyclohexylester;

[0535] 2-chloro-benzoic acid 4-hydroxy-4-(6-methoxy-naphthalen-2-yl)-3-(4-methyl; piperazin-1-ylmethyl)-cyclohexyl ester;

[0536] 3-chloro-benzoic acid 4-hydroxy-4-(6-methoxy-naphthalen-2-yl)-3-(4-methyl-piperazin-1-ylmethyl)-cyclohexyl ester;

[0537] 4-chloro-benzoic acid 4-hydroxy-4-(6-methoxy-naphthalen-2-yl)-3-(4-methyl-piperazin-1-ylmethyl)-cyclohexyl ester;

[0538] 2-fluoro-benzoic acid 4-hydroxy-4-(6-methoxy-naphthalen-2-yl)-3-(4-methyl-piperazin-1-ylmethyl)-cyclohexyl ester;

[0539] 3-fluoro-benzoic acid 4-hydroxy-4-(6-methoxy-naphthalen-2-yl)-3-(4-methyl-piperazin-1-ylmethyl)-cyclohexyl ester;

[0540] 4-fluoro-benzoic acid 4-hydroxy-4-(6-methoxy-naphthalen-2-yl)-3-(4-methyl-piperazin-1-ylmethyl)-cyclohexyl ester;

[0541] 2-methyl-benzoic acid 4-hydroxy-4-(6-methoxy-naphthalen-2-yl)-3-(4-methyl-piperazin-1-ylmethyl)-cyclohexyl ester;

[0542] 3-methyl-benzoic acid 4-hydroxy-4-(6-methoxy-naphthalen-2-yl)-3-(4-methyl-piperazin-1-ylmethyl)-cyclohexyl ester;

[0543] 4-methyl-benzoic acid 4-hydroxy-4-(6-methoxy-naphthalen-2-yl)-3-(4-methyl-piperazin-1-ylmethyl)-cyclohexyl ester;

[0544] 2-methoxy-benzoic acid 4-hydroxy-4-(6-methoxy-naphthalen-2-yl).-3-(4-methyl-piperazin-1-ylmethyl)-cyclohexyl ester;

[0545] 3-methoxy-benzoic acid 4-hydroxy-4-(6-methoxy-naphthalen-2-yl)-3-(4-methyl-piperazin-1-ylmethyl)-cyclohexyl ester;

[0546] 4-methoxy-benzoic acid 4-hydroxy-4-(6-methoxy-naphthalen-2-yl)-3-(4-methyl-piperazin-1-ylmethyl)-cyclohexyl ester;

[0547] 2,6-dichloro-benzoic acid 4-hydroxy-4-(6-methoxy-naphthalen-2-yl)-3-(4-methyl-piperazin-1-ylmethyl)-cyclohexyl ester;

[0548] 2,6-fluoro-benzoic acid 4-hydroxy-4-(6-methoxy-naphthalen-2-yl)-3-(4-methyl-piperazin-1-ylmethyl)-cyclohexyl ester;

[0549] 2-chloro-6-fluoro-benzoic acid 4-hydroxy-4-(6-methoxy-naphthalen-2-yl)-3-(4methyl-piperazin-1-ylmethyl)-cyclohexyl ester;

[0550] biphenyl-4-carboxylic acid 4-hydroxy-4-(6-methoxy-naphthalen-2-yl)-3-(4-methyl-piperazin-1-ylmethyl)-cyclohexyl ester;

[0551] 4-(2-chlorobenzyloxy)-2-(4-methyl-piperazin-1-ylmethyl)-1-naphthalen-2-ylcyclohexanol;

[0552] 4-(3-chlorobenzyloxy)-2-(4-methyl-piperazin-1-ylmethyl)-1-naphthalen-2-ylcyclohexanol;

[0553] 4-(4-chlorobenzyloxy)-2-(4-methyl-piperazin-1-ylmethyl)-1-naphthalen-2-yl-cyclohexanol;

[0554] 4-(2-fluorobenzyloxy)-2-(4-methyl-piperazin-1-ylmethyl)-1-naphthalen-2-ylcyclohexanol;

[0555] 4-(3-fluorobenzyloxy)-2-(4-methyl-piperazin-1-ylmethyl)-1-naphthalen-2-ylcyclohexanol;

[0556] 4-(4-fluorobenzyloxy)-2-(4-methyl-piperazin-1-ylmethyl)-1-naphthalen-2-ylcyclohexanol;

[0557] 4-(2-methyl-benzyloxy)-2-(4-methyl-piperazin-1-ylmethyl)-1-naphthalen-2-ylcyclohexanol;

[0558] 4-(3-methyl-benzyloxy)-2-(4-methyl-piperazin-1-ylmethyl)-1-naphthalen-2-yl-cyclohexanol;

[0559] 4-(4-methyl-benzyloxy)-2-(4-methyl-piperazin-1-ylmethyl)-1-naphthalen-2-yl-cyclohexanol;

[0560] 4-(2-methoxy-benzyloxy)-2-(4-methyl-piperazin-1-ylmethyl)-1-naphthalen-2-yl-cyclohexanol;

[0561] 4-(3-methoxy-benzyloxy)-2-(4-methyl-piperazin-1-ylmethyl)-1-naphthalen-2-yl-cyclohexanol;

[0562] 4-(4-methoxy-benzyloxy)-2-(4-methyl-piperazin-1-ylmethyl)-1-naphthalen-2-yl-cyclohexanol;

[0563] 4-(2,6-dichlorobenzyloxy)-2-(4-methyl-piperazin-1-ylmethyl)-1-naphthalen-2-yl-cyclohexanol;

[0564] 4-(2,6-difluorobenzyloxy)-2-(4-methyl-piperazin-1-ylmethyl)-1-naphthalen-2-yl-cyclohexanol;

[0565] 4-(2-chloro-6-fluorobenzyloxy)-2-(4-methyl-piperazin-1-ylmethyl)-1-naphthalen-2-yl-cyclohexanol;

[0566] 4-(2-chlorobenzyloxy)-1-(6-methoxy-naphthalen-2-yl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclohexanol;

[0567] 4-(3-chlorobenzyloxy)-1-(6-methoxy-naphthalen-2-yl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclohexanol;

[0568] 4-(4-chlorobenzyloxy)-1-(6-methoxy-naphthalen-2-yl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclohexanol;

[0569] 4-(2-fluorobenzyloxy)-1-(6-methoxy-naphthalen-2-yl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclohexanol;

[0570] 4-(3-fluorobenzyloxy)-1-(6-methoxy-naphthalen-2-yl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclohexanol;

[0571] 4-(4-fluorobenzyloxy)-1-(6-methoxy-naphthalen-2-yl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclohexanol;

[0572] 4-(2-methyl-benzyloxy)-1-(6-methoxy-naphthalen-2-yl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclohexanol;

[0573] 4-(3-methyl-benzyloxy)-1-(6-methoxy-naphthalen-2-yl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclohexanol;

[0574] 4-(4-methyl-benzyloxy)-1-(6-methoxy-naphthalen-2-yl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclohexanol;

[0575] 4-(2-methoxy-benzyloxy)-1-(6-methoxy-naphthalen-2-yl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclohexanol;

[0576] 4-(3-methoxy-benzyloxy)-1-(6-methoxy-naphthalen-2-yl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclohexanol;

[0577] 4-(4-methoxy-benzyloxy)-1-(6-methoxy-naphthalen-2-yl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclohexanol;

[0578] 4-(2,6-dichlorobenzyloxy)-1-(6-methoxy-naphthalen-2-yl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclohexanol;

[0579] 4-(2,6-difluorobenzyloxy)-1-(6-methoxy-naphthalen-2-yl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclohexanol;

[0580] 4-(2-chloro-6-fluorobenzyloxy)-1-(6-methoxy-naphthalen-2-yl)-2-(4-methyl-piperazin-1-yl-methyl)-cyclohexanol;

[0581] 2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-1-naphthalen-2-yl-cyclohexanol;

[0582] 4-fluoro-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(6-methoxynaphthalen-2-yl)-cyclohexylester;

[0583] 4-fluoro-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-naphthalen-2-yl-cyclohexylester;

[0584] 2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-1-(6-methoxy-naphthalen-2-yl)-cyclohexanol; and

[0585] 6-[2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-1-hydroxy-cyclohexyl]naphthalen-2-ol,

[0586] optionally in the form of their racemates, their pure stereoisomers, in particular enantiomers or diastereomers, or in the form of mixtures of stereoisomers, in particular the enantiomers or diastereomers, in any mixing ratio; in the illustrated form or in the form of their acids or their bases or in the form of their salts, in particular the physiologically acceptable salts, or in the form of their solvates, in particular the hydrates, in particular the hydrochloride salt or bishydrochloride salt.

[0587] The substances according to the invention are toxicologically safe, so they are suitable as a pharmaceutical active ingredient in pharmaceutical preparation. The invention also relates therefore to pharmaceutical preparations containing at least one substituted C-cyclohexylmethylamine derivative according to the invention, and optionally a suitable additive and/or auxiliary agent and/or optionally further active ingredient.

[0588] The pharmaceutical preparations according to the invention contain, in addition to at least one substituted C-cyclohexylmethylamine derivative according to the invention, optionally suitable additives and/or auxiliary agents, therefore also excipients, fillers, solvents, diluents, dyes and/or binders, and can be administered as pharmaceutical preparations in the form of injection solutions, drops or syrups, as semi-solid pharmaceutical preparations in the form of granules, tablets, pellets, patches, capsules, plasters or aerosols. The choice of auxiliary agents, etc. and the quantities thereof to be used depend on whether the pharmaceutical preparation is to be applied orally, perorally, parenterally, intravenously, intraperitoneally, intradermally, intramuscularly, intranasally, buccally, rectally or topically, for example to the skin, the mucus membranes or the eyes. Preparations in the form of tablets, dragees, capsules, granules, drops and syrups are suitable for oral application, solutions, suspensions, easily reconstitutable dry preparations and sprays are suitable for parenteral, topical and inhalative applications. Substituted C-cyclohexylmethylamine derivatives according to the invention in a deposit, in dissolved form or in a plaster, optionally with the addition of agents to promote skin penetration, are suitable percutaneous application preparations. Orally or percutaneously applicable preparation forms can release the substituted C-cyclohexylmethylamine derivatives according to the invention after a delay. In principle, other active ingredients known to the person skilled in the art can be added to the pharmaceutical preparations according to the invention.

[0589] The quantity of active ingredient to be administered to the patient varies as a function of the weight of the patient, the method of application, the indication and the severity of the illness. Conventionally, 0.005 to 1,000 mg/kg bodyweight, preferably 0.05 to 5 mg/kg of at least one substituted C-cyclohexylmethylamine derivative according to the invention are applied.

[0590] In a preferred form of the pharmaceutical preparation, a substituted C-cyclohexylmethylamine derivative is present as a pure diastereomer and/or enantiomer, as a racemate or as a non-equimolar or equimolar blend of the diastereomers and/or enantiomers.

[0591] The invention also relates to the use of a substituted C-cyclohexylmethylamine derivative according to the invention for producing a pharmaceutical composition for treating pain, in particular neuropathic or chronic pain. In this case it may be preferred if a substituted C-cyclohexylmethylamine derivative used is present as a pure diastereomer and/or enantiomer, as a racemate or as a non-equimolar or equimolar blend of the diastereomers and/or enantiomers.

[0592] The invention also relates to a method for producing a substituted C-cyclohexylmethylamine derivative according to the invention, as is recited in the following description and example.

[0593] Some methods for producing compounds according to the invention in accordance with formula I, which are analogously applied in this case, have already been described in DE 19547766 (I. Graudums et al, Grünenthal GmbH, 1995), which is herein incorporated by reference in its entirety. To produce substances according to formula I, in which A is not hydrogen, the methods described by Graudums et al. were combined with the methods known from the literature for producing substituted Mannich bases (Risch et al, Houben-Weyl—Methoden der Organischen Chemie, E21b (1995) 1925-1929; Angew. Chem. 106 (1994) 2531-2533; Synlett (1997) 974-976).

[0594] To produce substances according to the invention in which the olefins of partial formula Ia represent

[0595] tertiary alcohols,

[0596] optionally in a solvent or solvent mixture at temperatures between 20 and 120° C., are treated with organic or inorganic acids or other dehydrating agents such as acid halides. Formic acid or hydrogen bromides were preferably used. One of the abovementioned olefins is preferably or exclusively obtained in this manner, as a function of the selected reaction conditions.

[0597] From these olefins

[0598] compounds according to the invention are obtained by reduction of the CC double bond, whereby

[0599] is obtained. For this purpose, the olefins are preferably hydrogenated under a hydrogen atmosphere or also excess hydrogen pressure in the presence of a transition metal which was possibly bound to a carrier.

[0600] The reaction of tertiary alcohols

[0601] with hydrochloric acid at temperatures between −20 and +20° C. led to chlorine derivatives

[0602] During this reaction, the duration of the reaction, the concentration of the hydrochloric acid used and the use of an optionally added solvent has an influence on the course of the reaction. Under more drastic conditions, i.e. when using concentrated hydrochloric acid, long reaction times or the application of elevated temperatures, olefins

[0603] were also obtained.

[0604] The reaction of tertiary alcohols:

[0605] with fluorination reagents such as dimethylamino sulphur trifluoride (DAST) or Deoxofluor® led to fluorine derivatives

[0606] To produce substances according to the invention in which

[0607] is

[0608] were reacted with ammonia or ammonium salts, primary or secondary amines under reductive conditions. A large number of methods known from the literature is suitable for this purpose (see e.g., R. C. Larock; Comprehensive Organic Transformations; VCH Publishers; New York, Weinheim, Cambridge 1989). Complex hydrides such as sodium boron hydride, sodium cyanoboron hydride or particularly preferably sodium triacetoxyboron hydride were preferably used. If primary or secondary amines were obtained in this manner, they can be reacted with acid halides or acids to form amides using the methods known from the literature, alkalated with alkyl, aryl alkyl or heteroaryl alkyl halides using methods known from the literature or can be reductively aminated with aldehydes also using methods known from the literature (R. C. Larock; Comprehensive Organic Transformations; VCH Publishers; New York, Weinheim, Cambridge 1989).

[0609] The production of substances according to the invention in which

[0610] is

[0611] can be carried out using a large number of methods known from the literature (see e.g. R. C. Larock; Comprehensive Organic Transformations; VCH Publishers; New York, Weinheim, Cambridge 1989). For example, the ester

[0612] or the aldehyde

[0613] can be the starting point.

[0614] The ester

[0615] can be obtained using the above-described methods, starting from the commercially available cyclohexanone-4-carboxylic acid ether ester. The aldehyde

[0616] can be obtained from the ketone

[0617] for example by a Wittig reaction with methoxymethylphosphonium chloride or bromide and acid splitting of the initially formed enol ether (G. Wittig et al, Chem. Ber. 95 (1962) 2514-2525; S, O. Bhanot et al, J. Chem. Soc. C (1968) 2583-2588).

[0618] The invention also relates to a method for the treatment, in particular the treatment of pain, of non-human mammals or humans, that requires treatment of pain, in particular chronic pain, by administration of a therapeutically effective dose of a substituted C-cyclohexylmethylamine derivative according to the invention, or of a pharmaceutical preparation according to the invention.

[0619] The invention will be described further hereinafter by examples, but is not limited thereto.

EXAMPLES

[0620] The following examples show compounds according to the invention, their production and efficacy tests carried out therewith.

[0621] In general the following details apply:

[0622] The chemicals and solvents used were acquired commercially from conventional suppliers (Acros, Avocado, Aldrich, Fluka, Lancaster, Maybridge, Merck, Sigma, TCI etc.) or synthesized using methods well known to those ordinarily skilled in the art.

[0623] Analyses were made by NMR spectroscopy, ESI mass spectrometry and/or HPLC.

Grignard Reaction 1

[0624] Reaction Equation:

[0625] General Instruction 1 (AAV 1):

[0626] The reaction vessel was fully dried in the drying oven. The aryl iodide was introduced and 1 ml tetrahydrofuran (THF) added to it. Isopropyl magnesium chloride solution was added at −20° C. and the mixture stirred for 60 minutes before the Mannich base and further 0.25 ml THF were added. While stirring, the mixture was slowly allowed to thaw to ambient temperature and was restirred overnight. The mixture was then cooled to −20° C. again and hydrolyzed with ammonium chloride solution.

[0627] The reaction mixture was extracted three times with 3 ml ether in each case. The combined organic phases were dried by magnesium sulphate and evaporated at 40° C. under vacuum. Purification was effected by hydrochloride precipitation: dissolving the crude base in about 10 ml 2-butanone per gramme of base; addition of half a mol equivalent of water, followed by 1.1 mol equivalents of chlorotrimethylsilane and stirring overnight. If no hydrochloride formed even on cooling to about 4° C., the precipitation mixture was taken up in twice the volume of water, washed with three small portions of ether, the aqueous phase rendered alkaline with a little, about 30% sodium hydroxide solution and extracted three times with ether (“acid base extraction”). These last extracts were combined again and subjected to new hydrochloride precipitation. Batch A: R′ = H (Examples 1 to 28) 2.68 mmol (700 mg) Mannich base (1.22 M in THF) 5.36 mmol Aryl iodide (R-I) 4.02 mmol (2.01 ml) Isopropyl magnesium chloride solution (2 M in THF) 1.25 ml THF 2 ml 20% ammonium chloride solution and for the working up of ether and magnesium sulphate. Batch B: R′ = 4-F (Examples 29 to 50) 2.15 mmol (600 mg) Mannich base (1.00 M in THF) 4.30 mmol Aryl iodide (R-I) 3.22 mmol (1.61 ml) Isopropyl magnesium chloride solution (2 M in THF) 1.25 ml THF 2 ml 20% ammonium chloride solution and for the working up of ether and magnesium sulphate. Purifi- Ex- Yield cation ample (g hydro- (Acid base No. Aryl iodide chloride) extraction) 1 1-bromo-4-iodobenzene 0.190 2 1-iodo-4-trifluoromethyl-benzene 0.310 3 1,2-difluoro-4-iodobenzene 0.172 x 4 2-fluoro-4-iodotoluene 0.098 x 5 4-iodo-1,2-dichlorobenzene 0.340 6 1-iodonaphthalene 0.191 x 7 4-iodo-1,2-dimethylbenzene 0.246 x 8 2-fluoro-5-iodotoluene 0.167 x 9 4-fluoro-2-iodotoluene 0.148 x 10 1-chloro-2-fluoro-4-iodobenzene 0.151 x 11 4-chloro-2-iodoanisole 0.556 x 12 1-bromo-2-iodobenzene 0.208 x 13 2-iodoanisole 0.644 14 1-iodo-2-methylsulphanyl-benzene 0.665 15 1-chloro-4-iodobenzene 0.194 x 16 1-bromo-3-iodobenzene 0.152 x 17 1-bromo-2-fluoro-4-iodobenzene 0.287 x 18 4-iodoanisole 0.296 x 19 1-chloro-2-iodobenzene 0.218 x 20 1-iodo-3-trifluoromethyl-benzene 0.240 x 21 1-iodo-4-pentylbenzene 0.164 22 2-iodo-1,4-dimethylbenzene 0.084 x 23 1-iodo-4-isopropylbenzene 0.151 x 24 1-iodo-2,3-dimethylbenzene 0.127 x 25 1-fluoro-3-iodobenzene 0.195 x 26 1-iodo-3,5-bis(trifluoro-methyl)benzene 0.220 27 1-ethyl-4-iodobenzene 0.096 x 28 3,5-dichloro-5-iodobenzene 0.349 29 2-iodotoluene 0.083 x 30 4-iodotoluene 0.105 x 31 2-iodo-1,4-dimethylbenzene 0.089 32 4-iodo-1,2-dimethylbenzene 0.066 x 33 1-iodo-3,5-dimethylbenzene 0.098 34 1-iodo-4-isopropylbenzene 0.129 x 35 1-fluoro-3-iodobenzene 0.065 x 36 1-fluoro-4-iodobenzene 0.100 x 37 1,2-difluoro-4-iodobenzene 0.081 38 2-fluoro-4-iodotoluene 0.161 39 2-fluoro-5-iodotoluene 0.105 40 1-chloro-2-iodobenzene 0.077 41 1-chloro-3-iodobenzene 0.212 42 1-chloro-4-iodobenzene 0.107 43 1,2-dichloro-4-iodobenzene 0.255 44 1-chloro-2-fluoro-4-iodobenzene 0.092 45 1,3-dichloro-5-iodobenzene 0.183 46 4-chloro-2-iodoanisole 0.173 x 47 1-iodo-4-trifluormethyl-benzene 0.106 48 1-iodo-3,5-bis(trifluoro-methyl)benzene 0.087 49 2-iodoanisole 0.243 x 50 1-iodo-2-methylsulphanylbenzene 0.240 x

Grignard Reaction with Elimination 1

[0628] Reaction Equation:

[0629] Implementation: See AAV 1. Batch A: R′ = H (Example 51) Batch B: R′ = 4-F (Example 52) Purification Yield (Acid base Example No. Aryl iodide (g hydro-chloride) extraction) 51 2-iodothiophene 0.308 x 52 2-iodothiophene 0.102

[0630] Reaction Equation:

[0631] General Instruction 2 (AAV 2):

[0632] The apparatus was fully dried in the drying oven. The acid chloride was introduced and 1 ml dichloromethane added to it. Triethylamine was added at −10° C. and the mixture stirred for 20 minutes before the amine, dissolved in 4 ml dichloromethane, was added. While stirring, the mixture was slowly allowed to thaw to ambient temperature and restirred overnight.

[0633] At ambient temperature, diluted potassium hydroxide solution was added and the mixture subsequently centrifuged. The phases were separated, the organic phase dried by means of magnesium sulphate and evaporated at 40° C. under vacuum. Purification took place by hydrochloride precipitation, optionally after acid base extraction (see AAV 1). Batch A: (Example 53 to 62) 3.59 mmol (1.00 g) 4-amino-2-dimethylaminomethyl-1- (3-methoxyphenyl)cyclohexanol 5.39 mmol acid chloride (RCOCI) 9.74 mmol (1.36 ml) triethylamine 5 ml dichloromethane 2 ml potassium hydroxide solution (2 M) and for the working up of magnesium sulphate. Batch B: (Example 63 and 64) 2.16 mmol (600 g) 4-amino-2-dimethylaminomethyl-1-(3- methoxyphenyl)cyclohexanol 3.23 mmol acid chloride (RCOCI) 4.31 mmol (0.60 ml) triethylamine 3 ml dichloromethane 1.5 ml potassium hydroxide solution (2 M) and for the working up of magnesium sulphate. Yield Purification Example (g hydro- (Acid base No. Acid chloride chloride) extraction) 53 3,4-dichlorobenzoylchloride 0.627 54 2-naphthoylchloride 0.512 55 3-phenylpropionylchloride 0.119 56 4-nitrobenzoylchloride 0.975 57 4-methyl-3-nitrobenzoylchloride 0.656 58 3,4,5-trimethoxybenzoylchloride 0.236 x 59 4-chlorophenoxyacetylchloride 0.639 x 60 3-nitrobenzoylchloride 0.302 x 61 2-furoylchloride 0.746 x 62 phenoxyacetylchloride 0.527 x 63 4-(trifluormethyl)benzoyl-chloride 0.212 x 64 4-methoxybenzoylchloride 0.510 x

Grignard Reaction 2

[0634] Reaction Equation:

[0635] General Instruction 3 (AAV 3):

[0636] The apparatus was fully dried and aerated with nitrogen. The aryl iodide was introduced and 1 ml THF added to it. Isopropyl magnesium chloride solution was added at −20° C. and the mixture stirred for 60 minutes before the Mannich base and further 0.25 ml THF were added. While stirring, the mixture was slowly allowed to thaw to ambient temperature and was restirred overnight. The mixture was then cooled to −20° C. again and hydrolyzed with ammonium chloride solution.

[0637] The reaction mixture was extracted three times with 10 ml ether in each case. The combined organic phases were dried by magnesium sulphate and evaporated at 40° C. under vacuum. Purification was effected by column chromatography.

[0638] The purified product was then precipitated as hydrochloride and recrystallized (see AAV 1). Batch: (Example 65 to 97) 2.00 mmol (0.52 g) Mannich base (1.0 M in THF) 4.00 mmol aryl iodide (R-I) 3.00 mmol (1.73 ml) isopropyl magnesium chloride solution (2 M in THF) 1.25 ml THF 2 ml 20% ammonium chloride solution and for the working up of ether and magnesium sulphate. Yield (g hydro- Purification Example No. Aryl iodide chloride) Column chromatography Crystallisation 65* 1-fluoro-4-iodobenzene 0.134 ether/hexane/MeOH (25/25/1) 2-butanone/ether 66* 1-fluoro-4-iodobenzene 0.072 ether/hexane/MeOH (25/25/1) 2-butanone/ether 67 1-bromo-4-iodobenzene 0.154 ether/hexane/MeOH (25/25/1) 2-butanone/ether 68* 1-ethyl-4-iodobenzene 0.114 hexane/ethyl acetate/MeOH 2-butanone/ether (93/11) 69* 1-ethyl-4-iodobenzene 0.225 ether/hexane/MeOH (25/25/1) 2-butanone/ether 70 1-iodo-4-isopropyl- 0.093 ether/hexane/MeOH (25/25/1) 2-butanone/ether benzene 71* 4-iodoanisole 0.175 ether/hexane/MeOH (25/25/1) 2-butanone/ether 72* 4-iodoanisole 0.107 ether/hexane/MeOH (25/25/1) 2-butanone/ether 73 1-iodo-2,4-di- 0.136 ether/hexane/MeOH (25/25/1) 2-butanone/ether methylbenzene 74 1-iodo-2-methyl- 0.204 hexane/ethyl acetate/MeOH 2-butanone/ether sulphanyl-benzene (9/3/1) 75 4-fluoro-2-iodotoluene 0.136 ether/hexane/MeOH (25/25/1) 2-butanone/ether 76 2-iodo-1,4-di- 0.176 hexane/acetic-ester/MeOH 2-butanone/ether methylbenzene (12/3/1) 77 4-iodotoluene 0.140 ether/hexane/MeOH (25/25/1) 2-butanone/ether 78 1-fluoro-3-iodobenzene 0.126 hexane/ethyl acetate/MeOH 2-butanone/ether (12/3/1) 79 1-chloro-3-iodobenzene 0.255 ether/hexane/MeOH (25/25/1) 2-butanone/ether 80 1-chloro-2-fluoro-4- 0.110 ether/hexane/MeOH (25/25/1) 2-butanone/ether iodobenzene 81 1-iodo-3-tri- 0.220 ether/hexane/MeOH (25/25/1) 2-butanone/ether fluoromethyl-benzene 82 1,2-dichloro-5- 0.324 ether/hexane/MeOH (25/25/1) 2-butanone/ether iodobenzene 83 4-iodo-1,2- 0.170 ether/hexane/MeOH (25/25/1) 2-butanone/ether dimethylbenzene 84 1,2-dichloro-4- 0.390 ether/hexane/MeOH (25/25/1) 2-butanone/ether iodobenzene 85 1-chloro-4-iodobenzene 0.202 ether/hexane/MeOH (25/25/1) 2-butanone/ether 86 2-fluoro-4-iodotoluene 0.173 ether/hexane/MeOH (25/25/1) 2-butanone/ether 87 1-iodo-3,5- 0.083 ether/hexane/MeOH (25/25/1) 2-butanone/ether dimethylbenzene 88 1-bromo-2-fluoro-4- 0.096 ether/hexane/MeOH (25/25/1) 2-butanone/ether iodobeozene 89* 1-iodo-2,3- 0.145 ether/hexane/MeOH (25/25/1) 2-butanone/ether dimethylbenzene 90* 1-iodo-2,3- 0.096 ether/hexane/MeOH 25/2511 2-butanone/ether dimethylbenzene 91 1-iodo-naphthalene 0.082 ether/hexane/MeOH (25/25/1) 2-butanone/ether 92 1-iodo-3,5-bis- 0.168 ether/hexane/MeOH (25/25/1) 2-butanone/ether trifluoromethyl-benzene 93 1-bromo-3-iodobenzene 0.081 ether/hexane/MeOH 2-butanone/ether (250 5/1) 94 2-fluoro-5-iodotoluene 0.216 ether/hexane/MeOH 2-butanone/ether (25/25/1) 95* 3-iodotoluene 0.079 ether/hexane/MeOH 2-butanone/ether (25/25/1) 96* 3-iodotoluene 0.088 ether/hexane/MeOH 2-butanone/ether (25/25/1)

Grignard Reaction 3

[0639] Reaction Equation:

[0640] Implementation: See AAV 3. Batch A: R′ = H (Example 97 and 99) Batch B: R′ = 3-OCH₃ (Example 100 to 102) Batch C: R′ = 4-F (Example 103 and 104) Yield Ex- (g am- hydro- Purification ple chlor- Column No. Aryl iodide ide) chromatography Crystallisation  97 3-iodotoluene 0.033 ether/hexane/MeOH ether/ethyl acetate (25/25/1)  98 1,2-difluoro-4- 0.125 ether/hexane/MeOH ether/ethyl acetate iodobenzene (25/25/1)  99 4-iodotoluene 0.080 ether/hexane/MeOH ether/ethyl acetate (25/25/1) 100 4-iodotoluene 0.097 ether/hexane/MeOH ether/ethyl acetate (25/25/1) 101 1-chloro-4- 0.104 ether/hexane/MeOH ether/ethyl acetate iodobenzene (25/25/1) 102 -bromo-2- 0.101 ether/hexane/MeOH ether/ethyl acetate fluoro-4- (25/25/1) iodobenzene benzene 103 4-iodotoluene 0.080 ether/hexane/MeOH ether/ethyl acetate (25/25/1) 104 -chloro-4- 0.080 ether/hexane/MeOH ether/ethyl acetate iodobenzene OH (25/25/1)

Grignard Reaction with Elimination 2

[0641] Reaction Equation:

[0642] Implementation: See AAV 3. Ex- am- Yield Purification ple Aryl (g hydro- (column No. iodide chloride) chromatography) (crystallisation) 105 2-iodo-5- 0.122 ether/hexane/meOH 2-butanone/ether methyl- (25/25/1) thiophene

Elimination 1

[0643] Reaction Equation:

[0644] General Instruction 4 (AAV 4):

[0645] The tertiary alcohol was introduced and hydrobromic acid added to it. The mixture was stirred for 4 hours at an oil bath temperature of 80° C. (the mixture was optionally restirred overnight at ambient temperature). 40 g ice were then added to the mixture which was adjusted with sodium hydroxide solution to pH 10 to 11 with cooling, before it was extracted three times with about 20 ml ethyl acetate in each case. The organic phases were combined, dried with magnesium sulphate and evaporated under vacuum. The isomeric olefins were separated by column chromatography. The purified product was then precipitated as hydrochloride and recrystallized. Batch: (Example 106 to 110) 3.00 mmol tertiary alcohol (as hydrochloride) 30.0 ml 48% hydrobromic acid and for the working up of 32% sodium hydroxide solution and ethyl acetate. Ex- ample Yield Purification No. g hydrochloride column chromatography crystallisation 1,2 olefins: 106 0.050 ether/hexane/MeOH (25/25/1) MEK/ether 107 0.214 ether/hexane/MeOH (25/25/1) MEK/ether 108 0.074 ether/hexane/MeOH (25/25/1) MEK/ether 109 0.098 ether ethyl acetate/hexane/ MEK/ether MeOH (3/12/1) 1,6 olefins: 110 0.175 ether/hexane/MeOH (25/25/1) MEK/ether 111 0.027 ether/hexane/MeOH (25/25/1) MEK/ether 112 0.161 ether/hexane/MeOH (25/25/1) MEK/ether

Fluorination 1

[0646] Reaction Equation:

[0647] General Instruction 5 (AAV 5):

[0648] The apparatus was fully dried and aerated with nitrogen. 5 ml dichloromethane were then introduced and deoxofluorine added to it. The educt, dissolved in residual dichloromethane, was slowly added dropwise at a temperature of −5° C. and the mixture restirred for 90 minutes. While cooling some water was then added and the mixture adjusted to pH 11 by means of sodium carbonate solution. The mixture was then extracted three times with dichloromethane. The combined organic phases were dried by means of magnesium sulphate and evaporated under vacuum. Purification was effected by column chromatography. The purified product was then precipitated as hydrochloride and recrystallized. Batch: (Example 113) 1.50 mmol educt (tertiary alcohol) 5.00 mmol deoxofluorine 15 ml dichloromethane (dried) and for the working up of 32% sodium hydroxide solution and ethyl acetate. Purification Example Yield (column No. (g hydrochloride) chromatography) (crystallisation) 113 0.050 ether/hexane/MeOH MEK/ether (25/25/1)

Fluorination 2

[0649] Reaction Equation:

[0650] Implementation: See AAV 5: Ex- ample Yield Purification No. (g hydrochloride) (column chromatography) (crystallisation) 114 0.032 ethyl acetate ether

Grignard Reaction 4

[0651] Reaction Equation:

[0652] General Instruction 6 (AAV 6):

[0653] The Mannich base (400 μl, 0.5 M) dissolved in THF was introduced in a fully dried reaction vessel cooled under inert gas to −10° C. While stirring, two equivalents of the prepared Grignard or organolithium reagent were then added (0.5 M in THF or diethylether, 800 μl). The reaction mixture was stirred at ambient temperature. After three hours the mixture was cooled to −10° C. again and hydrolyzed with ammonium chloride solution.

[0654] The reaction mixture was extracted twice with ethyl acetate and evaporated at 40° C. under vacuum.

[0655] An ESI-MS was taken for characterization.

[0656] The Grignard or organolithium reagents used were produced from:

[0657] phenyl magnesium bromide

[0658] 4-chlorophenyl magnesium bromide

[0659] benzyl magnesium chloride

[0660] 4-fluoro-3-methylphenyl magnesium bromide

[0661] o-tolyl magnesium bromide

[0662] vinyl magnesium bromide

[0663] 4-t-butylphenyl magnesium bromide

[0664] cyclopentyl magnesium chloride

[0665] m-tolyl magnesium chloride

[0666] cyclohexyl magnesium chloride

[0667] 4-fluorophenyl magnesium bromide

[0668] phenethyl magnesium bromide

[0669] lithiumphenylacetylide

[0670] 2-thienyllithium

[0671] 1-bromomagnesium-2,4-dichlorbenzene

[0672] 3-bromoanisole magnesium bromide

[0673] phenylpropyl magnesium bromide

[0674] 2,3-dichlororphenyl magnesium bromide

[0675] p-toluyl magnesium bromide

[0676] 4-bromoanisole magnesium bromide

[0677] cyclohexylmethyl magnesium bromide

[0678] 2-bromomagnesium-4-fluoroanisole

[0679] 3-fluorophenyl magnesium bromide

[0680] 3-chlorophenyl magnesium bromide

[0681] 3,5-dichlororphenyl magnesium bromide

[0682] 2-chlorobenzyl magnesium chloride

[0683] 4-fluorobenzyl magnesium chloride

[0684] 3-methoxybenzyl magnesium chloride

[0685] 5-bromomagnesium-2-chlorobenzotrifluoroide

[0686] 3-fluorobenzyl magnesium chloride

[0687] 2-methoxyphenyl magnesium bromide

[0688] 2-methylbenzyl magnesium chloride

[0689] 3-chloro-4-fluorophenyl magnesium bromide

[0690] 3-bromomagnesiumbenzotrifluoroide

[0691] 3-methylbenzyl magnesium chloride

[0692] 4-chlorobenzyl magnesium chloride

[0693] 2-chloro-6-fluorobenzyl magnesium chloride

[0694] 2,5-dimethylbenzyl magnesium chloride

[0695] 3-chlorobenzyl magnesium chloride

[0696] 2,4-dichlororbenzyl magnesium chloride

[0697] 2-bromomethyl-1,4-dimethylbenzene

[0698] 4-bromo-1-chloro-2-trifluoromethylbenzene Example Name Calculated mass Ascertained mass 115 1-benzyl-2-(dimethylamino-phenyl-methyl)-4-phenyl- 399.57 400.4 cyclohexanol 116 2-(dimethyllamino-phenyl-methyl)-4-phenyl-1-vinyl- 335.49 336.3 cyclohexanol I 117 1-(4-tert-butyl-phenyl)-2-(dimethyl amino-phenyl-methyl)-4- 441.65 442.4 phenyl-cyclohexanol 118 2-(dimethyllamino-phenyl-methyl)-4-phenyl-1-m-tolyl- 399.57 400.3 cyclohexanol 119 2-(dimethylamino-phenyl-methyl)-1-phenethyl-4-phenyl- 413.6 414.5 cyclohexanol 120 2-(dimethyllamino-phenyl-methyl)-4-phenyl-1-phenylethynyl- 409.57 410.3 cyclohexanol 121 2-(dimethylamino-phenyl-methyl)-1-(3-methoxy-phenyl)-4- 415.57 416.3 phenyl-cyclohexanol 122 2-(dimethylamino-phenyl-methyl)-4-phenyl-1-(3-phenyl- 427.63 428.5 propyl)-cyclohexanol 123 2-(dimethylamino-phenyl-methyl)-1-(4-methoxy-phenyl)-4- 415.57 416.3 phenyl-cyclohexanol 124 2-(dimethylamino-phenyl-methyl)-1-(2-methoxy-phenyl)-4- 415.57 416.3 phenyl-cyclohexanol 125 4-benzyloxy-2-dimethylaminomethyl-1-phenyl-cyclohexanol 339.47 340.4 126 1-benzyl-4-benzyloxy-2-dimethylaminomethyl-cyclohexanol 353.5 354.4 127 4-benzyloxy-2-dimethylaminomethyl-1-(4-fluoro-3-methyl- 371.49 372.4 phenyl)-cyclohexanol 128 4-benzyloxy-2-dimethylaminomethyl-1-o-tolyl-cyclohexanol 353.5 354.4 129 4-benzyloxy-2-dimethylaminomethyl-1-vinyl-cyclohexanol 289.41 290.3 130 4-benzyloxy-1-cyclopentyl-2-dimethylaminomethyl- 331.49 332.4 cyclohexanol 131 4-benzyloxy-2-dimethylaminomethyl-1-m-tolyl-cyclohexanol 353.5 354.4 132 4-benzyloxy-2-dimethylaminomethyl-bicyclohexyl-1-ol 345.52 346.4 133 4-benzyloxy-2-dimethylaminomethyl-1-(4-fluoro-phenyl)- 357.46 358.3 cyclohexanol 134 4-benzyloxy-2-dimethylaminomethyl-1-phenylethynyl- 363.5 364.3 cyclohexanol 135 4-benzyloxy-2-dimethylaminomethyl-1-thiophen-2-yl- 345.5 346.4 cyclohexanol 136 4-benzyloxy-2-dimethylaminomethyl-1-(3-methoxy-phenyl)- 369.5 370.4 cyclohexanol 137 4-benzyloxy-2-dimethylaminomethyl-1-(3-phenyl-propyl)- 381.55 382.4 cyclohexanol 138 4-benzyloxy-2-dimethylaminomethyl-1-p-tolyl-cyclohexanol 353.5 354.4 139 4-benzyloxy-2-dimethylaminomethyl-1-(4-methoxy-phenyl)- 369.5 370.3 cyclohexanol 140 4-benzyloxy-2-dimethylaminomethyl-1-(3-fluoro- 357.46 358.4 phenyl)-cyclohexanol 141 4-benzyloxy-1-(3-chloro-phenyl)-2- 373.92 374.4 dimethylaminomethyl-cyclohexanol 142 4-benzyloxy-2-dimethylaminomethyl-1-(3-methoxy- 383.53 384.4 benzyl)-cyclohexanol 143 4-benzyloxy-1-(4-chloro-3-trifluoromethyl-phenyl)-2- 441.92 442.3 dimethylaminomethyl cyclohexanol 144 4-benzyloxy-2-dimethylaminomethyl-1-(3-fluorobenzyl)- 371.49 372.4 cyclohexanol 145 4-benzyloxy-2-dimethylaminomethyl-1-(2-methyl- 367.53 368.4 benzyl)-cyclohexanol 146 4-benzyloxy-2-dimethylaminomethyl-1-(2,5-dimethyl- 381.55 382.4 benzyl)-cyclohexanol 147 4-(4-chlorobenzyl)-2-dimethylaminomethyl-1-(3- 387.95 388.8 methoxy-phenyl)-cyclohexanol 148 4-(4-chlorobenzyl)-2-dimethylaminomethyl-1-(3-phenyl- 400 400.8 propyl)-cyclohexanol 149 4-(4-chlorobenzyl)-1-(2,3-dichlor-phenyl)-2- 426.81 427.0/428.9 dimethylaminomethyl-cyclohexanol 150 4-(4-chlorobenzyl)-1-cyclohexylmethyl-2- 377.99 378.8 dimethylaminomethyl-cyclohexanol 151 4-(4-chlorobenzyl)-2-dimethylaminomethyl-1-(5-fluoro-2- 405.94 406.7 metho-phenyl)-cyclohexanol 152 4-(4-chlorobenzyl)-2-dimethylaminomethyl-1-(3- 375.91 376.7 fluorophenyl)-cyclohexanol 153 4-(4-chlorobenzyl)-1-(3-chloro-phenyl)-2- 392.36 393.0 dimethylaminomethyl-cyclohexanol 154 4-(4-chlorobenzyl)-1-(3,5-dichloro-phenyl)-2- 426.81 426.5/428.3 dimethylaminomethyl-cyclohexanol 155 4-(4-chlorobenzyl)-1-(2-chlorobenzyl)-2- 406.39 406.9 dimethylaminomethyl-cyclohexanol 156 4-(4-chlorobenzyl)-2-dimethylaminomethyl-1-(4- 389.94 390.8 fluorobenzyl)-cyclohexanol 157 4-(4-chlorobenzyl)-2-dimethylaminomethyl-1-(3- 389.94 390.7 fluorobenzyl)-cyclohexanol 158 4-(4-chlorobenzyl)-2-dimethylaminomethyl-1-(2- 387.95 388.8 methoxy-phenyl)-cyclohexanol 159 4-(4-chlorobenzyl)-2-dimethylaminomethyl-1-(2-methyl- 385.97 386.8 benzyl)-cyclohexanol 160 4-(4-chlorobenzyl)-2-dimethylaminomethyl-1-(3-methyl- 385.97 386.7 benzyl)-cyclohexanol 161 1,4-bis-(4-chlorobenzyl)-2-dimethylaminomethyl- 406.39 407.1 cyclohexanol 162 4-(4-chlorobenzyl)-1-(2-chloro-6-fluorobenzyl)-2- 424.38 425.1 dimethylaminomethyl-cyclohexanol 163 4-(4-chlorobenzyl)-2-dimethylaminomethyl-1-(2,5- 400 400.8 dimethyl-benzy)1-cyclohexanol 164 4-(4-chlorobenzyl)-1-(3-chlorobenzyl)-2- 406.39 407.0 dimethylaminometh i-cyclohexanol 165 4-(4-chlorobenzyl)-1-(2,4-dichlorobenzyl)-2- 440.84 440.9/442.4 dimethylaminomethyl-cyclohexanol 166 4-(4-chlorobenzyl)-2-dimethylaminomethyl-1-phenyl- 357.92 358.5 cyclohexanol 167 4-(4-chlorobenzyl)-1-(4-chloro-phenyl)-2- 392.36 392.7/394.5 dimethylaminomethyl-cyclohexanol 168 4-(4-chlorobenzyl)-2-dimethylaminomethyl-1-(4-fluoro-3- 389.94 390.6 methyl-phenyl)-cyclohexanol 169 4-(4-chlorobenzyl)-2-dimethylaminomethyl-1-o-tolyl- 371.95 372.5 cyclohexanol 170 4-(4-chlorobenzyl)-2-dimethylaminomethyl-1-vinyl- 307.86 308.5 cyclohexanol 171 4-(4-chlorobenzyl)-1-cyclopentyl-2- 349.94 350.3 dimethylaminomethyl-cyclohexanol 172 4-(4-chlorobenzyl)-2-dimethylaminomethyl-1-m-tolyl- 371.95 372.5 cyclohexanol 173 4-(4-chlorobenzyl)-2-dimethylaminomethyl-bicyclohexyl- 363.97 364.4 1-ol 174 4-(4-chlorobenzyl)-2-dimethylaminomethyl-1-(4- 375.91 376.5 fluorophenyl)-cyclohexanol 175 4-(4-chlorobenzyl)-2-dimethylaminomethyl-1-phenethyl- 385.97 386.5 cyclohexanol 176 4-(4-chlorobenzyl)-2-dimethylaminomethyl-1- 381.94 382.5 phenylethynyl-cyclohexanol 177 4-(4-chlorobenzyl)-2-dimethylaminomethyl-1-thiophen-2- 363.95 364.4 yl-cyclohexanol 178 4-(4-chlorobenzyl)-2-dimethylaminomethyl-1--tolyl- 371.95 372.6 cyclohexanol 179 4-(4-chlorobenzyl)-2-dimethylaminomethyl-1-(4- 387.95 388.6 methoxy-phenyl)-cyclohexanol 180 4-(4-chlorobenzyl)-2-dimethylaminomethyl-1- 378.03 378.7 trimethylsilanylethynyl-cyclohexanol 181 4-(4-chlorobenzyl)-1-(4-chloro-3-trifluoromethyl-phenyl)- 460.36 460.8/462.1 2-dimethylaminomethyl-cyclohexanol 182 4-(4-chlorobenzyl)-1-(3-chloro-4-fluoro-phenyl)-2- 410.35 410.6/412.4 dimethylaminomethyl-cyclohexanol 183 4-(4-chlorobenzyl)-2-dimethylaminomethyl-1-(3- 425.92 426.6 trifluoromethyl-phenyl)-cyclohexanol 184 2-dimethylaminomethyl-4-(4-fluorobenzyl)-1--phenyl- 341.46 342.4 cyclohexanol 185 1-(4-chloro-phenyl)-2-dimethylaminomethyl-4-(4- 375.91 376.5 fluorobenzyl)-cyclohexanol 186 1-benzyl-2-dimethylaminomethyl-4-(4-fluoro-benzyl)- 355.49 356.4 cyclohexanol 187 2-dimethylaminomethyl-4-(4-fluorobenzyl)-1-(4-fluoro-3- 373.48 374.4 methyl-phenyl)-cyclohexanol 188 2-dimethylaminomethyl-4-(4-fluorobenzyl)-1-o-tolyl- 355.49 356.4 cyclohexanol 189 2-dimethylaminomethyl-4-(4-fluorobenzyl)-1-vinyl- 291.4 292.3 cyclohexanol 190 1-(4-tert-butyl-phenyl)-2-dimethylaminomethyl-4-(4- 397.57 398.4 fluorobenzyl)-cyclohexanol 191 1-cyclopentyl-2-dimethylaminomethyl-4-(4- 333.49 334.5 fluorobenzyl)-cyclohexanol 192 2-dimethylaminomethyl-4-(4-fluorobenzyl)-1-m-tolyl- 355.49 356.3 cyclohexanol 193 2-dimethylaminomethyl-4-(4-fluorobenzyl)-bic clohexyl- 347.51 348.4 1-ol 194 2-dimethylaminomethyl-4-(4-fluorobenzyl)-1-(4- 359.45 360.4 fluorophenyl)-cyclohexanol 195 2-dimethylaminomethyl-4-(4-fluorobenzyl)-1-phenethyl- 369.52 370.4 cyclohexanol 196 2-dimethylaminomethyl-4-(4-fluorobenzyl)-1- 365.49 366.3 phenylethynyl-cyclohexanol 197 2-dimethylaminomethyl-4-(4-fluorobenzyl)-1-thiophen-2- 347.49 348.3 yl-cyclohexanol 198 2-dimethylaminomethyl-4-(4-fluorobenzyl)-1-(3-methoxy- 371.49 372.3 phenyl)-cyclohexanol 199 2-dimethylaminomethyl-4-(4-fluorobenzyl)-1-(3-phenyl- 383.55 384.4 propyl)-cyclohexanol1-(2,3-dichlorophenyl)-2- 200 dimethylaminomethyl-4-(4-fluorobenzyl)-cyclohexanol 410.35 410.6/412.4 201 2-dimethylaminomethyl-4-(4-fluorobenzyl)-1-p-tolyl- 355.49 356.4 cyclohexanol 202 2-dimethylaminomethyl-4-(4-fluorobenzyl)-1-(4-methoxy- 371.49 372.3 phenyl)-cyclohexanol 203 1-cyclohexylmethyl-2-dimethylaminomethyl-4-(4- 361.54 362.4 fluorobenzyl)-cyclohexanol 204 2-dimethylaminomethyl-4-(4-fluorobenzyl)-1-(5-fluoro-2- 389.48 390.4 methoxy-phenyl)-cyclohexanol 205 2-dimethylaminomethyl-4-(4-fluorobenzyl)-1-(3- 359.45 360.4 fluorophenyl)-cyclohexanol 206 1-(3-chlorophenyl)-2-dimethylaminomethyl-4-(4- 375.91 376.5/377.5 fluorobenzyl)-cyclohexanol 207 1-(3,5-dichloro-phenyl)-2-dimethylaminomethyl-4-(4- 410.35 410.6/412.3 fluorobenzyl)-cyclohexanol 208 1-(2-chlorobenzyl)-2-dimethylaminomethyl-4-(4-fluoro- 389.94 390.7 benzy)-cyclohexanol 209 2-dimethylaminomethyl-1,4-bis-(4-fluoro-benzyl- 373.48 374.5 cyclohexanol 210 2-dimethylaminomethyl-4-(4-fluorobenzyl)-1-(3-methoxy- 385.52 386.4 benzyl)-cyclohexanol 211 1-(4-chloro-3-trifluoromethyl-phenyl)-2- 443.91 444.5/445.4 dimethylaminomethyl-4-(4-fluorobenzyl)-cyclohexanol 212 2-dimethylaminomethyl-4-(4-fluorobenzyl)-1-3-fluorobenzyl- 373.48 374.4 cyclohexanol 213 2-dimethylaminomethyl-4-(4-fluorobenzyl)-1-2-methoxy- 371.49 372.4 phenyl-cyclohexanol 214 2-dimethylaminomethyl-4-(4-fluorobenzyl)-1-2-methyl- 369.52 370.4 benzyl-cyclohexanol 215 1-(3-chloro-4-fluoro-phenyl)-2-dimethylaminomethyl-4-(4- 393.9 394.5 fluorobenzyl)-cyclohexanol 216 2-dimethylaminomethyl-4-(4-fluorobenzyl)-1-(3- 409.46 410.5 trifluoromethyl-phenyl)-cyclohexanol 217 2-dimethylaminomethyl-4-(4-fluorobenzyl)-1-(3-methyl- 369.52 370.4 benzyl)-cyclohexanol 218 1-(4-chlorobenzyl)-2-dimethylaminomethyl-4-4-fluorobenzyl- 389.94 390.5 cyclohexanol 219 1-(2-chloro-6-fluorobenzyl)-2-dimethylaminomethyl-4-(4- 407.93 408.5 fluorobenzyl) cyclohexanol 220 2-dimethylaminomethyl-1-(2,5-dimethyl-benzyl-4-(4- 383.55 384.4 fluorobenzyl)-cyclohexanol 221 1-(3-chlorobenzyl)-2-dimethylaminomethyl-4-(4- 389.94 390.4/391.3 fluorobenzyl)-cyclohexanol 222 1-(2,4-dichlorobenzyl)-2-dimethylaminomethyl-4-(4- 424.38 424.5/426.3 fluorobenzyl)-cyclohexanol 223 2-dimethylaminomethyl-4-(3-methoxy-benzyl)-1-phenyl- 353.5 354.5 cyclohexanol 224 1-benzyl-2-dimethylaminomethyl-4-(3-methoxy-benzyl)- 367.53 368.6 cyclohexanol 225 2-dimethylaminomethyl-1-(4-fluoro-3-methyl-phenyl)-4-(3- 385.52 386.4 methoxy-benzyl)-cyclohexanol 226 2-dimethylaminomethyl-4-(3-methoxy-benzyl)-1-o-tolyl- 367.53 368.5 cyclohexanol 227 2-dimethylaminomethyl-4-(3-methoxy-benzyl)-1-vinyl- 303.44 304.3 cyclohexanol 228 1-(4-tert-butyl-phenyl)-2-dimethylaminomethyl-4-(3- 409.61 410.7 methoxy-benzyl)--Cyclohexanol 229 1-cyclopentyl-2-dimethylaminomethyl-4-(3-methoxy-benzyl- 345.52 346.4 cyclohexanol 230 2-dimethylaminomethyl-4-(3-methoxy-benzyl)-1-m-tolyl- 367.53 368.4 cyclohexanol 231 2-dimethylaminomethyl-4-(3-methoxy-benzyl)-biclohexyl-1- 359.55 360.4 ol 232 2-dimethylaminomethyl-4-(3-methoxy-benzyl)-1-phenethyl- 381.55 382.4 cyclohexanol 233 2-dimethylaminomethyl-4-(3-methoxy-benzyl)-1- 377.52 378.4 phenylethynyl-cyclohexanol 234 2-dimethylaminomethyl-4-(3-methoxy-benzyl)-1-thiophen-2- 359.53 360.3 I-cyclohexanol 235 2-dimethylaminomethyl-4-(3-methoxy-benzyl-1-(3- 383.53 384.4 methoxy-phenyl-cyclohexanol 236 2-dimethylaminomethyl-4-(3-methoxy-benzyl)-1-(3- 395.58 396.6 phenyl-propyl-cyclohexanol 237 1-(2,3-dichloro-phenyl)-2-dimethylaminomethyl-4-(3- 422.39 422.8/424.5 methoxy-benzyl)-cyclohexanol 238 2-dimethylaminomethyl-4-(3-methoxy-benzyl)-1-tolyl- 367.53 368.5 cyclohexanol 239 1-cyclohexylmethyl-2-dimethylaminomethyl-4-(3- 373.58 374.8 methoxy-benzyl)-cyclohexanol 240 2-dimethylaminomethyl-1-(5-fluoro-2-methoxy-phenyl)- 401.52 402.5 4-(3-methoxy-benzyl) cyclohexanol 241 1-(3-chloro-phenyl)-2-dimethylaminomethyl-4-(3- 387.95 388.5 methoxy-benzyl)-cyclohexanol 242 1-(3,5-dichloro-phenyl)-2-dimethylaminomethyl-4-(3- 422.39 422.7/424.5 methoxy-benzyl)-cyclohexanol 243 1-(4-chloro-3-trifluoromethyl-phenyl)-2- 455.94 456.6/457.4 dimethylaminomethyl-4-(3-methoxy-benzyl)-cyclohexanol 244 2-dimethylaminomethyl-1-(3-fluorobenzyl)-4-(3-methoxy- 385.52 386.4 benzyl)-cyclohexanol 245 2-dimethylaminomethyl-4-(3-methoxy-benzyl)-1-(2- 383.53 384.4 methoxy-phenyl)-cyclohexanol 246 2-dimethylaminomethyl-4-(3-methoxy-benzyl)-1-(3- 421.5 422.6 trifluoromethyl-phenyl)-Cyclohexanol 247 1-(2-chloro-6-fluorobenzyl)-2-dimethyl aminomethyl-4- 419.96 420.9/422.6 (3-methoxy-benzyl)-Cyclohexanol 248 2-dimethylaminomethyl-1-(2,5-dimethyl-benzyl)-4-(3- 395.58 396.7 methoxy-benzyl)-cyclohexanol 249 1-(3-chlorobenzyl)-2-dimethylaminomethyl-4-(3- 401.97 402.9 methoxy-benzyl)-cyclohexanol 250 2-dimethylaminomethyl-4-(4-fluoro-benzyloxy)-1- 357.46 358.4 phenyl-cyclohexanol 251 1-benzyl-2-dimethylaminomethyl-4-(4-fluoro-benzyloxy)- 371.49 372.8 cyclohexanol 252 2-dimethylaminomethyl-4-(4-fluoro-benzyloxy)-1-(4- 389.48 390.4 fluoro-3-methyl-phenyl)--cyclohexanol 253 2-dimethylaminomethyl-4-(4-fluoro-benzyloxy)-1-vinyl- 307.4 308.6 cyclohexanol 254 1-(4-tert-butyl-phenyl)-2-dimethylaminomethyl-4-(4- 413.57 414.6 fluorobenzyloxy)-cyclohexanol 255 1-cyclopentyl-2-dimethyl aminomethyl-4-(4- 349.48 350.4 fluorobenzyloxy)-cyclohexanol 256 2-dimethylaminomethyl-4-(4-fluoro-benzyloxy)-1-m- 371.49 372.5 tolyl-cyclohexanol 257 2-dimethylaminomethyl-4-(4-fluoro-benzyloxy)- 363.51 364.6 bicyclohexyl-1-ol 258 2-dimethylaminomethyl-4-(4-fluoro-benzyloxy-1- 385.52 386.5 phenethyl-cyclohexanol 259 2-dimethylaminomethyl-4-(4-fluoro-benzyloxy)-1- 381.49 382.6 phenylethynyl-cyclohexanol 260 2-dimethylaminomethyl-4-(4-fluoro-benzyloxy)-1- 363.49 364.6 thiophen-2-yl-cyclohexanol 261 2-dimethylaminomethyl-4-(4-fluoro-benzyloxy)-1-(3- 387.49 388.6 methoxy-phenyl)-cyclohexanol 262 2-dimethylaminomethyl-4-(4-fluoro-benzyloxy)-1-p- 371.49 372.6 tolyl-cyclohexanol 263 1-cyclohexylmethyl-2-dimethylaminomethyl-(4-4- 377.54 379.0 fluorobenzyloxy)-cyclohexanol 264 2-dimethylaminomethyl-1-(3-fluorobenzyl)-4-(4- 389.48 390.7 fluorobenzyloxy)-cyclohexanol 265 2-dimethylaminomethyl-4-(4-fluoro-benzyloxy)-1-(2- 387.49 388.8 methoxy-phenyl)-cyclohexanol 266 2-dimethylaminomethyl-4-(4-fluoro-benzyloxy-1-3- 385.52 387.0 methyl-benzyl-cyclohexanol 267 2-dimethylaminomethyl-1-(2,5-dimethyl-benzyl--(4- 399.54 400.9 fluorobenzyloxy-cyclohexanol 268 1-(3-chlorobenzyl)-2-dimethylaminomethyl-4-(4- 405.94 406.8 fluorobenzyloxy-cyclohexanol 340 4-benzyloxy-2-dimethylaminomethyl-1-(3-phenyl-propyl) cyclohexanol; hydrochloride 341 2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-1-(3-phenyl-propyl)- cyclohexanol; hydrochloride 342 2-dimethylaminomethyl-1-(3-fluorobenzyl)-4-(4-fluorobenzyloxy)- cyclohexanol; hydrochloride 343 4-benzyloxy-2-dimethylaminomethyl-1-3-fluorobenzyl-cyclohexanol; hydrochloride 344 2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-1-p-tolyl-cyclohexanol; hydrochloride 345 4-benzyloxy-2-dimethylaminomethyl-1-p-tolyl-cyclohexanol; hydrochloride 346 2-dimethylaminomethyl-1-(2,5-dimethyl-benzyl)-4-(4-fluorobenzyloxy)- cyclohexanol; hydrochloride 347 4-benzyloxy-2-dimethylaminomethyl-1-(2,5-dimethyl-benzyl)- cyclohexanol; hydrochloride 348 1-(4-chloro-3-trifluoromethyl-phenyl)-2-dimethylaminomethyl-4-(4-fluoro benzyloxy)-cyclohexanol; hydrochloride 349 4-benzyloxy-1-(4-chloro-3-trifluoromethyl-phenyl)-2 dimethylaminomethyl-cyclohexanol; hydrochloride

Alkylation

[0699] Reaction Equation:

[0700] General Instruction 7 (AAV 7):

[0701] 360 mg 3-dimethylaminomethyl-4-(3-methoxyphenyl)cyclohexanol hydrochloride were introduced into 3 ml THF p.a., 340 mg potassium-tert.-butylate (2.5 mol equivalents) added and restirred for 15 minutes. The correspondingly substituted benzyl bromide (1.5 mol equivalents) was then dissolved in 0.6 ml THF p.a., added dropwise and restirred for 16 hours at ambient temperature.

[0702] For working up, 2.2 ml water were added, the mixture then extracted twice with 10 ml ethyl acetate in each case, the combined extracts dried by sodium sulphate, filtered and concentrated. The crude products were chromotographed on silica gel with ethyl acetate/methanol/hexane (V/V/V=1:1:1). The products obtained were converted with chlorotrimethylsilane in aqueous 2-butanone into the corresponding hydrochlorides in the same way as in AAV 1.

[0703] When producing [5-(4-methoxybenzyloxy)-2-(3-methoxyphenyl)cyclohexylmethyl]-dimethylamine, the cyclohexene derivative [5-(4-methoxybenzyloxy)-2-(3-methoxyphenyl)cyclohex-2-enylmethyl]dimethylamine was isolated as a secondary product, as the 3-dimethylaminomethyl-4-(3-methoxyphenyl)cyclohexanol hydrochloride used was contaminated by the preliminary stage 5-dimethylaminomethyl-4-(3-methoxyphenyl)-cyclohex-3-enol hydrochloride which was catalytically hydrogenated by palladium to produce 3-dimethylaminomethyl-4-(3-methoxyphenyl)cyclohexanol.

[0704] Examples according to AAV 7: 269 [5-benzyloxy-2-(3-methoxy-phenyl)-cyclohexylmethyl]-dimethyl-amine; hydrochloride 270 [5-(3-chlorobenzyloxy)-2-(3-methoxy-phenyl)-cyclohexylmethyl]- dimethyl-amine; hydrochloride 271 [2-(3-methoxy-phenyl)-5-(naphthalen-2-ylmethoxy)-cyclohexylmethyl]- dimethyl-amine; hydrochloride 272 [5-(3-methoxy-benzyloxy)-2-(3-methoxy-phenyl)-cyclohexylmethyl]- dimethyl-amine; hydrochloride 273 [5-(4-chlorobenzyloxy)-2-(3-methoxy-phenyl)-cyclohexylmethyl]- dimethyl-amine; hydrochloride 274 [5-(4-methoxy-benzyloxy)-2-(3-methoxy-phenyl)-cyclohexylmethyl]- dimethyl-amine; hydrochloride 275 2-dimethylaminomethyl-1-(3-methoxy-phenyl)-4-(naphthalen-2- ylmethoxy)-cyclohexanol; hydrochloride 276 [5-(4-methoxy-benzyloxy)-2-(3-methoxy-phenyl)-cyclohex-2- enylmethyl]-dimethyl-amine; hydrochloride

Alkylation 2

[0705] Reaction Equation:

[0706] General Instruction 9 (AAV 8):

[0707] 5 ml of a 0.5 M solution of potassium-tert.-butylate were introduced in THF p.a. in the dried reaction vessel, 2 ml of a 1 M solution of the respective alcohol in THF p.a. added at −10° C., stirred for 30 minutes with heating to ambient temperature, cooled to −10° C. again, 2 ml of a 1.25 M solution of the corresponding acid chloride added in THF p.a. and stirred for 1 hour at 30° C.

[0708] For working up, 2 ml 1M sodium hydrogen carbonate solution was added at 0° C., the supernatant THF phase separated, chromatographed on silica gel with diisopropyl ether/methanol (V/V=1/1) and the product obtained converted by dissolution in 2-butanone and addition of water and chlorotrimethylsilane into the hydrochloride in the same way as in AAV 1.

[0709] Mixtures according to AAV 8 with 2-dimethylaminomethyl-1-(3-methoxyphenyl)cyclohexane-1,4-diol hydrochloride (equatorial alcohol): 282 2,2-dimethyl-propionic acid 3-dimethylaminomethyl-4-hydroxy-4- (3-methoxy-phenyl)-cyclohexylester; hydrochloride 281 3-methoxy-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3- methoxy-phenyl)-cyclohexylester; hydrochloride 280 4-methoxy-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3- methoxy-phenyl)-cyclohexylester; hydrochloride 307 2-methoxy-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3- methoxy-phenyl)-cyclohexylester; hydrochloride 306 naphthalene-1-carboxylic acid 3-dimethylaminomethyl-4-hydroxy- 4-(3-methoxy-phenyl)-cyclohexylester; hydrochloride 305 3,5-dimethoxy-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4- (3-methoxy-phenyl)-cyclohexylester; hydrochloride 304 3,4,5-trimethoxy-benzoic acid 3-dimethylaminomethyl-4-hydroxy- 4-(3-methoxy-phenyl)-cyclohexylester; hydrochloride 303 phenyl-acetic acid 3-dimethylaminomethyl-4-hydroxy-4-(3- methoxy-phenyl)-cyclohexylester; hydrochloride 302 (3-methoxy-phenyl)-acetic acid 3-dimethylaminomethyl-4- hydroxy-4-(3-methoxy-phenyl)-cyclohexylester; hydrochloride 301 (4-methoxy-phenyl)-acetic acid 3-dimethylaminomethyl-4- hydroxy-4-(3-methoxy-phenyl-cyclohexylester; hydrochloride 300 cyclopentancarboxylic acid 3-dimethylaminomethyl-4-hydroxy-4- (3-methoxy-phenyl)-cyclqhexyl ester; hydrochloride 299 2-fluoro-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3- methoxy-phenyl)-cyclohexylester; hydrochloride 298 3-fluoro-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3- methoxy-phenyl)-cyclohexylester; hydrochloride 297 4-fluoro-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3- methoxy-phenyl)-cyclohexylester; hydrochloride 296 3,5-difluoro-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3- methoxy-phenyl)-cyclohexylester; hydrochloride 295 4-trifluoromethyl-benzoic acid 3-dimethylaminomethyl-4-hydroxy- 4-(3-methoxy-phenyl)-cyclohexylester; hydrochloride 294 2-chloro-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3- methoxy-phenyl)-cyclohexylester; hydrochloride 293 3-chloro-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3- methoxy-phenyl)-cyclohexylester; hydrochloride 292 4-chloro-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3- methoxy-phenyl)-cyclohexylester; hydrochloride 291 3,4-dichloro-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3- methoxy-phenyl)-cyclohexylester; hydrochloride 290 4-methyl-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3- methoxy-phenyl)-cyclohexylester; hydrochloride 309 2-hydroxy-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3- methoxy-phenyl)-cyclohexylester; hydrochloride 289 naphthalene-2-carboxylic acid 3-dimethylaminomethyl-4-hydroxy- 4-(3-methoxy-phenyl)-cyclohexylester; hydrochloride 287 3,4-dimethoxy-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4- (3-methoxy-phenyl)-cyclohexylester; hydrochloride 336 valeric acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy- phenyl)-cyclohexylester; hydrochloride

[0710] Mixtures according to AAV 8 with 2-dimethylaminomethyl-1-(3-methoxyphenyl)cyclohexane-1,4-diol hydrochloride (axial alcohol): 277 butyric acid 3-dimethyl aminomethyl-4-hydroxy-4-(3-methoxy- phenyl)-cyclohexylester; hydrochloride 286 2,2-dimethyl-propionic acid 3-dimethylaminomethyl-4-hydroxy-4- (3-methoxy-phenyl)-cyclohexylester; hydrochloride 285 3-methoxy-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3- methoxy-phenyl)-cyclohexylester; hydrochloride 284 4-methoxy-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3- methoxy-phenyl)-cyclohexylester; hydrochloride 327 2-methoxy-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3- methoxy-phenyl)-cyclohexylester; hydrochloride 326 naphthalene-1-carboxylic acid 3-dimethylaminomethyl-4-hydroxy- 4-(3-methoxy-phenyl)-cyclohexylester; hydrochloride 325 3,5-dimethoxy-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4- (3-methoxy-phenyl)-cyclohexylester; hydrochloride 324 3,4,5-trimethoxy-benzoic acid 3-dimethylaminomethyl-4-hydroxy- 4-3-methoxy-phenyl)-cyclohexylester; hydrochloride 323 phenyl-acetic acid 3-dimethyl aminomethyl-4-hydroxy-4-(3- methoxy-phenyl)-cyclohexylester; hydrochloride 322 (3-methoxy-phenyl)-acetic acid 3-dimethylaminomethyl-4- hydroxy-4-3-methoxy-phenyl)-cyclohexylester; hydrochloride 321 (4-methoxy-phenyl)-acetic acid 3-dimethylaminomethyl-4- hydroxy-4-3-methoxy-phenyl)-cyclohexylester; hydrochloride 320 cyclopentane carboxylic acid 3-dimethylaminomethyl-4-hydroxy- 4-(3-methoxy-phenyl)-cyclohexylester; hydrochloride 319 2-fluoro-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3- methoxy-phenyl)-cyclohexylester; hydrochloride 318 3-fluoro-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3- methoxy-phenyl)-cyclohexylester; hydrochloride 317 4-fluoro-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3- methoxy-phenyl)-cyclohexylester; hydrochloride 316 3,5-difluoro-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3- methoxy-phenyl)-cyclohexylester; hydrochloride 315 4-trifluoromethyl-benzoic acid 3-dimethylaminomethyl-4-hydroxy- 4-(3-methoxy-phenyl)-cyclohexylester; hydrochloride 314 2-chloro-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3- methoxy-phenyl)-cyclohexylester; hydrochloride 313 3-chloro-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3- methoxy-phenyl)-cyclohexylester; hydrochloride 312 4-chloro-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3- methoxy-phenyl)-cyclohexylester; hydrochloride 311 3,4-dichloro-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3- methoxy-phenyl)-cyclohexylester; hydrochloride 310 4-methyl-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3- methoxy-phenyl)-cyclohexylester; hydrochloride 308 naphthalene-2-carboxylic acid 3-dimethylaminomethyl-4-hydroxy- 4-(3-methoxy-phenyl)-cyclohexylester; hydrochloride 288 3,4-dimethoxy-benzoic acid 3-dimethyl aminomethyl-4-hydroxy-4- (3-methoxy-phenyl)-cyclohexylester; hydrochloride

Example 278 4-amino-2-dimethylaminomethyl-1-(3-methoxyphenyl)cyclohexanol Dihydrochloride

[0711] 2.43 g dry zinc chloride were introduced in portions and while stirring into a solution of 2.64 g sodium cyanoboronhydride in 45 ml dried methanol and subsequently stirred for 30 minutes. This solution was slowly added dropwise to a suspension of 16.7 g dry ammonium acetate and 9.0 g 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxyphenyl)cyclohexanone in 45 ml dry methanol and subsequently stirred for 72 hours at ambient temperature.

[0712] For working up, 45 ml semi-concentrated hydrochloric acid were added dropwise in the ice bath, subsequently stirred for 1 hour after addition had finished and the methanol was removed under vacuum. 30 g potassium hydroxide were added to the residue with ice cooling and the mixture was extracted three times with 25 ml dichloromethane in each case, the combined extracts dried by potassium carbonate, filtered and concentrated. The isolated crude product (8.8 g) was chromotographised on silica gel. The 6.25 g of 4-amino-2-dimethylaminomethyl-1-(3-methoxyphenyl)cyclohexanol obtained were converted into the corresponding dihydrochloride in the same way as in AAV 1.

Examples 334 and 335 2-dimethylaminomethyl-1-(3-methoxyphenyl)-4-methylamino-cyclohexanol Dihydrochloride (Equatorial and Axial Amine)

[0713] 18.8 g 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxyphenyl)cyclohexanone were dissolved in 210 ml THF p.a. under a nitrogen atmosphere, 24.3 ml 5.6 M methyl amine solution in THF added to the ice/methanol bath, followed by 5.72 ml glacial acetic acid and a total of 20.0 g sodium triacetoxyborhydride added in portions. After the additions had finished the cooling bath was removed and the mixture subsequently stirred for 16 hours with heating to ambient temperature.

[0714] For working up, 120 ml sodium hydroxide solution were added, the mixture extracted three times with 100 ml diethyl ether in each case, the extracts combined, washed twice with 50 ml water in each case, dried by sodium sulphate, filtered and concentrated. 2.5 g of the crude product obtained (17.4 g) were chromotographised with methanol on silica gel. 580 or 600 mg of two diastereomer 2-dimethyl-aminomethyl-1-(3-methoxyphenyl)-4-methylaminocyclohexanols were obtained which corresponded to the axial and the equatorial product and these were converted into the corresponding dihydrochlorides in the same way as in AAV 1.

Example 279 2-dimethylaminomethyl-1-(3-methoxyphenyl)-4-(naphthalen-2-ylmethoxy)cyclohexanol Hydrochloride

[0715] 2-dimethylaminomethyl-1-(3-methoxyphenyl)-4-(naphthalen-2-ylmethoxy)-cyclohexanol and the corresponding hydrochloride were produced in the same way as in AAV 7 from 2-dimethylaminomethyl-1-(3-methoxyphenyl)cyclohexane-1,4-diol hydrochloride and 2-bromomethylnaphthalene.

Example 350 (2,5-bis-(4-fluorobenzyloxy)-2-(3-methoxyphenyl)-cyclohexylmethyl]-dimethylamine Hydrochloride

[0716] When reacting 2-dimethylaminomethyl-1-(3-methoxyphenyl)-cyclohexane-1,4-diol hydrochloride with 4-fluorobenzylbromide in accordance with AAV 7, (2,5-bis-(4-fluorobenzyloxy)-2-(3-methoxyphenyl)-cyclohexylmethyl]-dimethylamine was also obtained as a secondary product after chromatographic purification on silica gel, which was converted into the corresponding hydrochloride in the same way as in AAV 1.

Example 283 Butyric Acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxyphenhyl)-cyclohexylester Hydrochloride

[0717] 28.0 g 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxyphenhyl)cyclohexanone were dissolved in 140 ml isopropanol under a nitrogen atmosphere, 1.72 g sodium tetrahydridoborate were added in portions and the mixture subsequently stirred for 1 hour. For working up, initially 91 ml 2 M hydrochloric acid were added, then 20 ml 10 M sodium hydroxide solution were added, the mixture extracted twice with 100 ml dichloromethane in each case, the combined extracts dried by sodium sulphate, filtered and concentrated. The crude product obtained (29.8 g) was dissolved in 500 ml acetone and by addition of 1.82 ml water, followed by 12.7 ml chlorotrimethylsilane and stirring overnight converted into 25.7 g 2-dimethylaminomethyl-1-(3-methoxyphenyl)cyclohexane-1,4-diol hydrochloride (equatorial alcohol). After adding 2 M sodium carbonate solution and extracting twice with ethyl acetate, 5.6 g of the enriched diastereoisomer reduction product could be isolated from the mother liquor, and this was purified by chromatography on silica gel with ethyl acetate/methanol (V/V=1:3). After hydrochloride precipitation, 4.1 g 2-dimethylaminomethyl-1-(3-methoxyphenyl)cyclohexane-1,4-diol hydrochloride (axial alcohol) were obtained.

[0718] 205 g 2-dimethylaminomethyl-1-(3-methoxyphenyl)cyclohexane-1,4-diol hydrochloride (equatorial alcohol) were suspended in 2,050 ml THF p.a. under a nitrogen atmosphere, 149 g potassium-tert.-butylate were slowly added, the mixture stirred for 1 hour, 71 ml butyrylchloride added dropwise and the mixture stirred for a further hour, before 36 g potassium-tert.-butylate and 34 ml butyryl chloride were again added. For working up, 980 ml water were added, the mixture extracted twice with 1,000 ml ethyl acetate in each case, the combined extracts washed with a little 1 M sodium hydrogen carbonate solution, dried by magnesium sulphate, filtered and concentrated. The crude product obtained (236 g) was combined with a further, analogously produced charge of this crude product (232 g), dissolved in 2,400 ml acetone and 470 ml dry ethanol and by adding half a mol equivalent of water and a mol equivalent of chlorotrimethylsilane, 442 g of the hydrochloride of butyric acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxyphenyl)cyclohexylester were obtained.

Examples 332 and 333 (+)- and (−)-butyric Acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxyphenyl)cyclohexylester

[0719] The enantiomers (+)- and (−)-butyric acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxyphenyl)cyclohexylester were produced by enzymatic resolution of racemates of butyric acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxyphenyl)cyclohexylester and subsequent isolation of the remaining butyrate and repeated esterification of the 2-dimethylaminomethyl-1-(3-methoxyphenyl)cyclohexane-1,4-diols obtained, as described for the racemate (Gais, Hans-Joachim; Griebel, Carsten; Buschmann, Helmut; Tetrahedron: Asymmetry 11 (2000) 917-928).

Example 351 5-dimethylaminomethyl-4-(3-methoxyphenyl)-cyclohex-3-enol Hydrochloride

[0720] 20.0 g 2-dimethylaminomethyl-1-(3-methoxyphenyl)cyclohexane-1,4-diol (equatorial alcohol) were dissolved in 300 ml concentrated formic acid, 6.75 ml acetyl chloride were added and the mixture heated for two hours to reflux. After cooling the mixture was concentrated, the residue taken up with 2 M sodium hydroxide solution and extracted with ethyl acetate. The combined extracts were dried by sodium sulphate, filtered, concentrated, the crude product obtained (16.7 g) dissolved in 2-butanone and by addition of 1.15 ml water and 8.1 ml chlorotrimethylsilane 5-dimethylaminomethyl-4-(3-methoxyphenyl)-cyclohex-3-enol hydrochloride (17.7 g) precipitated.

Examples 328 and 329 2-dimethylaminomethyl-1,4-bis-(3-methoxyphenyl)-cyclohexane-1,4-diol Hydrochloride (Cis- and Trans-Diol)

[0721] The corresponding Grignard reagent was produced in 60 ml THF p.a. from 7.47 g magnesium and 38.9 ml 3-bromoanisole, a solution of 40 g 1,4-dioxa-spiro[4.5]decan-8-one added dropwise in 75 ml THF p.a. at about 10° C. and subsequently stirred for 1 hour. For working up, 20 mass percent ammonium chloride solution was added to the ice bath, extracted with ethyl acetate, the combined extracts dried by sodium sulphate, filtered and concentrated. 128 ml water, 62 g ice and a solution of 31.5 ml concentrated hydrochloric acid in 385 ml were added to the crude product obtained (61.6 g) in the ice bath, the mixture stirred for five hours at 5 to 10° C., extracted with ethyl acetate, the combined extracts dried by sodium sulphate, filtered and concentrated. The crude product was mixed with diisopropyl ether and the remaining solids filtered off. 14.0 g 4-hydroxy-4-(3-methoxyphenyl)cyclohexanone were obtained.

[0722] 4.23 g dimethylmethylene ammonium chloride and a drop of acetyl chloride were added in 100 ml acetonitrile to 10.0 g 4-hydroxy-4-(3-methoxyphenyl)cyclohexanone and the mixture stirred for 16 hours. The precipitated solid was filtered off, washed with a little acetonitrile and dried under vacuum. 12.2 g 2-dimethylaminomethyl-4-hydroxy-4-(3-methoxyphenyl)-cyclohexanone were obtained.

[0723] The corresponding Grignard reagent was obtained in 20 ml THF p.a. from 0.75 g magnesium and 3.9 ml 3-bromoanisole, a solution of 3.87 g 2-dimethylaminomethyl-4-hydroxy-4-(3-methoxyphenyl)cyclohexanone added dropwise in 25 ml THF p.a. added dropwise at about 10° C. and the mixture stirred for 1 hour. For working up, 20 mass percent ammonium chloride solution was added in the ice bath, extracted with ethyl acetate, the combined extracts dried by sodium sulphate, filtered and concentrated. The crude product (5.44 g) obtained was chromatographed with ethyl acetate/methanol (V/V=1:1) on silica gel. The diastereomer 2-dimethylaminomethyl-1,4-bis-(3 methoxyphenyl)-cyclohexane-1,4-diols (cis- and trans-diol) obtained were converted with chlorotrimethylsilane in aqueous 2-butanone into the corresponding hydrochlorides (240 and 777 mg) in the same way as in AAV 1.

Examples 337 and 338 (E)- and (Z)-[3-dimethylaminomethyl-4-hydroxy-4-(3-methoxyphenyl)cyclohexyl-iden] Ethyl Acetate Hydrochloride

[0724] 100 g 1,4-dioxa-spiro[4.5]decan-8-one were dissolved in 800 ml toluene, 534 ml 32 mass percent sodium hydroxide solution were added, a solution of 127 ml triethylphosphonoacetate added dropwise in 250 ml toluene with ice cooling and intensive stirring and the mixture subsequently stirred for 1 hour. The organic phase was separated off, the aqueous phase extracted with toluene, the combined organic phases washed three times with water, dried by sodium sulphate, filtered and concentrated. The crude product obtained was chromatographed with diisopropylether/hexane (V/V=1:1) on silica gel. 92.9 g (1,4-dioxa-spiro[4.5]dec-8-ylidene) ethyl acetate were obtained.

[0725] 92.8 g (1,4-dioxa-spiro[4.5]dec-8-ylidene) ethyl acetate were dissolved in 465 ml diisopropyl ether, 186 ml water and 137 ml concentrated hydrochloric acid added, stirred for 1 hour, the phases separated, the aqueous phase extracted twice with diisopropyl ether, the combined organic phases dried by sodium sulphate, filtered and concentrated. The crude product obtained (95.9 g) was chromatographed with diisopropyl ether/hexane (V/V=2:1) on silica gel. In addition to 17.2 g of unreacted (1,4-dioxa-spiro[4.5]dec-8-ylidene) ethyl acetate, 76.3 g (4-oxocyclohexylidene) ethyl acetate were obtained.

[0726] 7.5 g dimethylmethylene ammonium chloride were added to 87.6 g (4-oxocyclohexylidene) ethyl acetate in 260 ml acetonitrile, heated for 1 hour to 60° C., 250 ml diisopropyl ether added and the mixture stirred overnight at ambient temperature. The precipitated solids were filtered off, washed with a little acetonitrile and dried under vacuum. 30.4 g (E)-(3-dimethylaminomethyl-4-oxocyclo-hexylidene) ethyl acetate were obtained. The mother liquor was concentrated to dryness and the residue (95 g) recrystallized from 475 ml 20-butanone. 62.3 g (Z)-(3-dimethylaminomethyl-4-oxocyclohexylidene) ethyl acetate were obtained.

[0727] The corresponding Grignard reagent was produced in 10 ml THF p.a. from 0.37 g magnesium and 1.9 ml 3-bromoanisole, a solution of 2.40 g (Z)-(3-dimethylaminomethyl-4-oxocyclohexylidene) ethyl acetate in 24 ml THF p.a. added dropwise with ice cooling and subsequently stirred for 1 hour. For working up, 5 ml 4 M ammonium chloride solution were added in the ice bath, the organic phase separated off, the aqueous phase extracted twice with ethyl acetate, the combined organic phases dried by sodium sulphate, filtered and concentrated. The crude product obtained (3.20 g) was chromatographed with diisopropyl ether/methanol (V/V=1:1) on silica gel. 1.61 g (Z)-[3-dimethylaminomethyl-4-hydroxy-4-(3-methoxyphenyl)cyclohexylidene) ethyl acetate were obtained and converted into the corresponding hydrochloride in the same was as in AAV 1. In the same way, 1.48 g of the hydrochloride of (E)-[3-dimethylaminomethyl-4-hydroxy-4-(3-methoxyphenyl)cyclohexylidene) ethyl acetate were produced from 2.40 g (E)-)-(3-dimethylaminomethyl-4-oxocyclohexylidene) ethyl acetate.

Example 352 2-dimethylaminomethyl-1-(6-methoxynaphthalen-2-yl)cyclohexane-1,4-diol Hydrochloride

[0728] The corresponding Grignard reagent was produced in 720 ml THF p.a. from 18.2 g magnesium and 177 g 2-bromo-6-methoxynaphthalene, a solution of 105 g 7-dimethylaminomethyl-1,4-dioxa-spiro[4.5]decan-8-one in 315 ml THF p.a. added dropwise with ice cooling and the mixture subsequently stirred for 1 hour. For working up, 375 ml 4 M ammonium chloride solution were added to the ice bath, the organic phase separated off, the aqueous phase extracted twice with ethyl acetate, the combined organic phases dried by sodium sulphate, filtered and concentrated. 229 g 7-dimethylaminomethyl-8-(6-methoxynaphthalen-2-yl)-1,4-dioxa-spiro[4.5]decan-8-ole were obtained.

[0729] 229 g 7-dimethylaminomethyl-8-(6-methoxynaphthalen-2-yl)-1,4-dioxa-spiro[4.5]decan-8-ol were dissolved in 1,150 ml THF, 164 ml water and 41 ml concentrated hydrochloric acid added, the mixture stirred for five hours, neutralised with 32 mass percent sodium hydroxide solution, extracted twice with ethyl acetate/THF (V/V=1:1), the combined organic phases washed twice with saturated sodium chloride solution, dried by magnesium sulphate, filtered and concentrated. 400 ml methanol and 600 ml diisopropylether were added to the crude product obtained (196 g) the mixture filtered, the filtrate concentrated, dissolved in 1,600 ml 2-butanone and the hydrochloride precipitated by adding water and chlorotrimethylsilane in the same way as in AAV 1. 106 g of hydrochloride of 3-dimethylaminomethyl-4-hydroxy-4-(6-methoxynaphthalen-2-yl)cyclohexanone were obtained.

[0730] 4.3 g sodium tetrahydridoborate were introduced into 82 ml ethanol p.a., 82.2 g 3-dimethyl-minomethyl-4-hydroxy-4-(6-methoxynaphthalen-2-yl)cyclohexanone, dissolved in 330 ml ethanol p.a., added dropwise with ice cooling, and stirred for 1 hour. For working up, initially 44 ml concentrated hydrochloric acid, then 40 ml 32 mass percent sodium hydroxide solution were added with ice cooling, the mixture extract twice with dichloromethane, the combined organic phases dried by magnesium sulphate, filtered and concentrated. 77.4 g of the hydrochloride of 2-dimethylaminomethyl-1-(6-methoxynaphthalen-2-yl)cyclohexane-1,4-diol were obtained from the crude product obtained (88.2 g) in the same way as in AAV 1.

Example 353 Butyric Acid 3-dimethylaminomethyl-4-hydroxy-4-(6-methoxynaphthalen-2-yl)cyclohexyl Ester Hydrochloride

[0731] 70.0 g 2-dimethylaminomethyl-1-(6-methoxynaphthalen-2-yl)cyclohexane-1,4-diol were suspended in 560 ml THF p.a., 44.0 g potassium-tert.-butylate added in portions, the mixture stirred for 20 minutes, 21.0 ml butyryl chloride added dropwise, the mixture stirred for a further 20 minutes and a further 21.0 g potassium-tert.-butylate and 20.0 ml butyryl chloride respectively added again twice in accordance with the above model. For working up, 290 ml water were added with ice bath cooling, the phases separated, the mixture extracted once with ethyl acetate, the combined organic phases washed with 1 M sodium hydrogen carbonate solution, dried by magnesium sulphate, filtered and concentrated. 47.1 g of the hydrochloride of butyric acid 3-dimethylaminomethyl-4-hydroxy-4-(6-methoxynaphthalen-2-yl)cyclohexyl ester were obtained from the crude product obtained (90 g) in the same way as in AAV 1.

Example 331 4-benzyloxy-2-dimethylaminomethyl-1-(6-methoxynaphthalen-2-yl)cyclohexanol Hydrochloride

[0732] The corresponding Grignard reagent was produced in 11 ml THF p.a. from 0.28 g magnesium and 2.72 g 2-bromo-6-methoxynaphthalene, a solution of 2.00 g 4-benzyloxy-2-dimethylaminomethylcyclohexanone in 8 ml THF p.a. added dropwise with ice cooling, and the mixture stirred for 1 hour. For working up, 4 ml 4 M ammonium chloride solution were added to the ice bath, the organic phase separated off, the aqueous phase extracted twice with diethyl ether, the combined organic phases dried by sodium sulphate, filtered and concentrated. The crude product obtained (3.20 g) was chromatographed with ethyl acetate/methanol/hexane (V/V/V=1:1:1) on silica gel. 1.52 g 4-benzyloxy-2-dimethylaminomethyl-1-(6-methoxynaphthalen-2-yl)cyclohexanol were obtained and converted into the corresponding hydrochloride (1.32 g) in the same way as in AAV 1.

Example 330 6-(4-benzyloxy-2-dimethylaminomethyl-1-hydroxy-cyclohexyl)-naphthalen-2-ol Hydrochloride

[0733] 200 g 6-bromonaphthalen-2-ol, 143 g imidazole and 151 g tert.-butylchlorodimethylsilane were dissolved in 1,000 ml dimethylformamide, stirred for two hours at ambient temperature, the solution largely concentrated (506 g), the residue dissolved in ethyl acetate and water, 1,500 ml saturated sodium chloride solution added, the phases separated, the aqueous phase extracted twice with ethyl acetate and the organic phases combined and concentrated. The crude product obtained was dissolved in boiling hexane and subsequently kept overnight at 4° C. After filtration, 158 g (6-bromonaphthalen-2-yloxy)-tert.-butyldimethylsilane were isolated. Repeated concentration of the mother liquor and recrystallisation from methanol yielded a further 54 g (6-bromonaphthalen-2-yloxy)-tert.-butyldimethylsilane.

[0734] 3.87 g (6-bromonaphthalen-2-yloxy)-tert.-butyldimethylsilane were dissolved in 19 ml THF p.a., 6.0 ml 1.6 M butyl lithium solution in hexane added dropwise with dry ice cooling, briefly stirred, then a solution of 2.00 g 4-benzyloxy-2-dimethylaminomethylcyclohexanone in 20 ml THF p.a. added dropwise and stirred for 1 hour while slowly heating. For working up, 4 ml water were added to the ice bath, the organic phase separated, the aqueous phase extracted twice with diethyl ether, the combined organic phases dried by sodium sulphate, filtered and concentrated. The crude product obtained (5.00 g) was chromatographed with ethyl acetate/methanol (V/V=1:1) on silica gel. 2.20 g 6-(4-benzyloxy-2-dimethylaminomethyl-1-hydroxy-cyclohexyl)-naphthalen-2-ol were obtained and converted into the corresponding hydrochloride (1.33 g) in the same way as in AAV 1.

[0735] General Supplement to the Examples:

[0736] By way of supplement, the following further examples were produced by at least one of the above (basic) methods or AAVs: Example No.: Compound name: 354 benzoic acid 4-hydroxy-3-(4-methyl-piperazin-1-ylmethyl)-4- naphthalen-2-yl-cyclohexyl ester; bis-hydrochloride 355 2-chloro-benzoic acid 4-hydroxy-3-(4-methyl-piperazin-1-ylmethyl)-4- naphthalen-2-yl-cyclohexyl ester; bis-hydrochloride 356 3-chloro-benzoic acid 4-hydroxy-3-(4-methyl-piperazin-1-ylmethyl)-4- naphthalen-2-yl-cyclohexyl ester; bis-hydrochloride 357 4-chloro-benzoic acid 4-hydroxy-3-(4-methyl-piperazin-1-ylmethyl)-4- naphthalen-2-yl-cyclohexyl ester; bis-hydrochloride 358 2-fluoro-benzoic acid 4-hydroxy-3-(4-methyl-piperazin-1-ylmethyl)-4- naphthalen-2-yl-cyclohexyl ester; bis-hydrochloride 359 3-fluoro-benzoic acid 4-hydroxy-3-(4-methyl-piperazin-1-ylmethyl) 4-naphthalen-2-yl-cyclohexyl ester; bis-hydrochloride 360 4-fluoro-benzoic acid 4-hydroxy-3-(4-methyl-piperazin-1-ylmethyl) 4-naphthalen-2-yl-cyclohexyl ester; bis-hydrochloride 361 2-methyl-benzoic acid 4-hydroxy-3-(4-methyl-piperazin-1-ylmethyl) 4-naphthalen-2-yl-cyclohexyl ester; bis-hydrochloride 362 3-methyl-benzoic acid 4-hydroxy-3-(4-methyl-piperazin-1-ylmethyl) 4-naphthalen-2-yl-cyclohexyl ester; bis-hydrochloride 363 4-methyl-benzoic acid 4-hydroxy-3-(4-methyl-piperazin-1-ylmethyl) 4-naphthalen-2-yl-cyclohexyl ester; bis-hydrochloride 364 2-methoxy-benzoic acid 4-hydroxy-3-(4-methyl-piperazin-1- ylmethyl)-4-naphthalen-2-yl-cyclohexyl ester; bis-hydrochloride 365 3- methoxy -benzoic acid 4-hydroxy-3-(4-methyl-piperazin-1- ylmethyl)-4-naphthalen-2-yl-cyclohexyl ester; bis-hydrochloride 366 4- methoxy -benzoic acid 4-hydroxy-3-(4-methyl-piperazin-1- ylmethyl)-4-naphthalen-2-yl-cyclohexyl ester; bis-hydrochloride 367 2,6-dichloro-benzoic acid 4-hydroxy-3-(4-methyl-piperazin-1- ylmethyl)-4-naphthalen-2-yl-cyclohexyl ester; bis-hydrochloride 368 2,6-difluoro-benzoic acid 4-hydroxy-3-(4-methyl-piperazin-1- ylmethyl)-4-naphthalen-2-yl-cyclohexyl ester; bis-hydrochloride 369 2-chloro-5-fluoro-benzoic acid 4-hydroxy-3-(4-methyl-piperazin-1- ylmethyl)-4-naphthalen-2-yl-cyclohexyl ester; bis-hydrochloride 370 biphenyl-4-carboxylic acid 4-hydroxy-3-(4-methyl-piperazin-1-ylmethyl) 4-naphthalen-2-yl-cyclohexylester; bis-hydrochloride 371 2-chloro-benzoic acid 4-hydroxy-4-(6-methoxy-naphthalen-2-yl)-3-(4- methyl-piperazin-1-ylmethyl)-cyclohexyl ester; bis-hydrochloride 372 3-chloro-benzoic acid 4-hydroxy-4-(6-methoxy-naphthalen-2-yl)-3-(4- methyl-piperazin-1-ylmethyl)-cyclohexyl ester; bis-hydrochloride 373 4-chloro-benzoic acid 4-hydroxy-4-(6-methoxy-naphthalen-2-yl)-3-(4- methyl-piperazin-1-ylmethyl)-cyclohexyl ester; bis-hydrochloride 374 2-fluoro-benzoic acid 4-hydroxy-4-(6-methoxy-naphthalen-2-yl)-3-(4- methyl-piperazin-1-ylmethyl)-cyclohexyl ester; bis-hydrochloride 375 3-fluoro-benzoic acid 4-hydroxy-4-(6-methoxy-naphthalen-2-yl)-3-(4- methyl-piperazin-1-ylmethyl)-cyclohexyl ester; bis-hydrochloride 376 4-fluoro-benzoic acid 4-hydroxy-4-(6-methoxy-naphthalen-2-yl)-3-(4- methyl-piperazin-1-ylmethyl)-cyclohexyl ester; bis-hydrochloride 377 2-methyl-benzoic acid 4-hydroxy-4-(6-methoxy-naphthalen-2-yl)-3-(4- methyl-piperazin-1-ylmethyl)-cyclohexyl ester; bis-hydrochloride 378 3-methyl-benzoic acid 4-hydroxy-4-(6-methoxy-naphthalen-2- methyl-piperazin-1-ylmethyl)-cyclohexyl ester; bis-hydrochloride 379 4-methyl-benzoic acid 4-hydroxy-4-(6-methoxy-naphthalen-2-yl)-3-(4- methyl-piperazin-1-ylmethyl)-cyclohexyl ester; bis-hydrochloride 380 2-methoxy-benzoic acid 4-hydroxy-4-(6-methoxy-naphthalen-2-yl)-3- (4-methyl-piperazin-1-ylmethyl)-cyclohexyl ester; bis-hydrochloride 381 3-methoxy-benzoic acid 4-hydroxy-4-(6-methoxy-naphthalen-2-yl)-3- (4-methyl-piperazin-1-ylmethyl)-cyclohexyI ester; bis-hydrochloride 382 4-methoxy-benzoic acid 4-hydroxy-4-(6-methoxy-naphthalen-2-yl)-3- (4-methyl-piperazin-1-ylmethyl)-cyclohexyl ester; bis-hydrochloride 383 2,6-dichloro-benzoic acid 4-hydroxy-4-(6-methoxy-naphthalen-2-yl)-3- (4-methyl-piperazin-1-ylmethyl)-cyclohexyl ester; bis-hydrochloride 384 2,6-fluoro-benzoic acid 4-hydroxy-4-(6-methoxy-naphthalen-2-yl)-3-(4- methyl-piperazin-1-ylmethyl)-cyclohexyl ester; bis-hydrochloride 385 2-chloro-6-fluoro-benzoic acid 4-hydroxy-4-(6-methoxy-naphthalen-2- yl)-3-(4-methyl-piperazin-1-ylmethyl)-cyclohexyl ester; bis-hydrochloride 386 biphenyl-4-carboxylic acid 4-hydroxy-4-(6-methoxy-naphthalen-2-yl)-3- (4-methyl-piperazin-1-ylmethyl)-cyclohexyl ester; bis-hydrochloride 387 4-(2-chlorobenzyloxy)-2-(4-methyl-piperazin-1-ylmethyl)-1- naphthalen-2-yl-cyclohexanol; bis-hydrochloride 388 4-(3-chlorobenzyloxy)-2-(4-methyl-piperazin-1-ylmethyl)-1- naphthalen-2-yl-cyclohexanol; bis-hydrochloride 389 4-(4-chlorobenzyloxy)-2-(4-methyl-piperazin-1-ylmethyl)-1- naphthalen-2-yl-cyclohexanol; bis-hydrochloride 390 4-(2-fluorobenzyloxy)-2-(4-methyl-piperazin-1-ylmethyl)-1-naphthalen 2-yl-cyclohexanol; bis-hydrochloride 391 4-(3-fluorobenzyloxy)-2-(4-methyl-piperazin-1-ylmethyl)-1-naphthalen 2-yl-cyclohexanol; bis-hydrochloride 392 4-(4-fluorobenzyloxy)-2-(4-methyl-piperazin-1-ylmethyl)-1-naphthalen 2-yl-cyclohexanol; bis-hydrochloride 393 4-(2-methyl-benzyloxy)-2-(4-methyl-piperazin-1-ylmethyl)-1- naphthalen-2-yl-cyclohexanol; bis-hydrochloride 394 4-(3-methyl-benzyloxy)-2-(4-methyl-piperazin-1-ylmethyl)-1- naphthalen-2-yl-cyclohexanol; bis-hydrochloride 395 4-(4-methyl-benzyloxy)-2-(4-methyl-piperazin-1-ylmethyl)-1- naphthalen-2-yl-cyclohexanol; bis-hydrochloride 396 4-(2-methoxy-benzyloxy)-2-(4-methyl-piperazin-1-ylmethyl)-1- naphthalen-2-yl-cyclohexanol; bis-hydrochloride 397 4-(3-methoxy-benzyloxy)-2-(4-methyl-piperazin-1-ylmethyl)-1- naphthalen-2-yl-cyclohexanol; bis-hydrochloride 398 4-(4-methoxy-benzyloxy)-2-(4-methyl-piperazin-1-ylmethyl)-1- naphthalen-2-yl-cyclohexanol; bis-hydrochloride 399 4-(2,6-dichlorobenzyl)-2-(4-methyl-piperazin-1-ylmethyl)-1- naphthalen-2-yl-cyclohexanol, bis-hydrochloride 400 4-(2,6-difluorobenzyloxy)-2-(4-methyl-piperazin-1-ylmethyl)-1- naphthalen-2-yl-cyclohexanol, bis-hydrochloride 401 4-(2-chloro-6-fluorobenzyloxy)-2-(4-methyl-piperazin-1-ylmethyl)-1- naphthalen-2-yl-cyclohexanol, bis-hydrochloride 402 4-(2-chlorobenzyloxy)-1-(6-methoxy-naphthalen-2-yl)-2-(4-methyl piperazin-1-ylmethyl)-cyclohexanol; bis-hydrochloride 403 4-(3-chlorobenzyloxy)-1-(6-methoxy-naphthalen-2-yl)-2-(4-methyl piperazin-1-ylmethyl)-cyclohexanol; bis-hydrochloride 404 4-(4-chlorobenzyloxy)-1-(6-methoxy-naphthalen-2-yl)-2-(4-methyl piperazin-1-ylmethyl)-cyclohexanol; bis-hydrochloride 405 4-(2-fluorobenzyloxy)-1-(6-methoxy-naphthalen-2-yl)-2-(4-methyl piperazin-1-ylmethyl)-cyclohexanol; bis-hydrochloride 406 4-(3-fluorobenzyloxy)-1-(6-methoxy-naphthalen-2-yl)-2-(4-methyl piperazin-1-ylmethyl)-cyclohexanol; bis-hydrochloride 407 4-(4-fluorobenzyloxy)-1-(6-methoxy-naphthalen-2-yl)-2-(4-methyl piperazin-1-ylmethyl)-cyclohexanol; bis-hydrochloride 408 4-(2-methyl-benzyloxy)-1-(6-methoxy-naphthalen-2-yl)-2-(4-methyl piperazin-1-ylmethyl)-cyclohexanol; bis-hydrochloride 409 4-(3-methyl-benzyloxy)-1-(6-methoxy-naphthalen-2-yl)-2-(4-methyl piperazin-1-ylmethyl)-cyclohexanol; bis-hydrochloride 410 4-(4-methyl-benzyloxy)-1-(6-methoxy-naphthalen-2-yl)-2-(4-methyl piperazin-1-ylmethyl)-cyclohexanol; bis-hydrochloride 411 4-(2-methoxy-benzyloxy)-1-(6-methoxy-naphthalen-2-yl)-2-(4-methyl piperazin-1-ylmethyl)-cyclohexanol; bis-hydrochloride 412 4-(3-methoxy-benzyloxy)-1-(6-methoxy-naphthalen-2-yl)-2-(4-methyl piperazin-1-ylmethyl)-cyclohexanol; bis-hydrochloride 413 4-(4-methoxy-benzyloxy)-1-(6-methoxy-naphthalen-2-yl)-2-(4-methyl piperazin-1-ylmethyl)-cyclohexanol; bis-hydrochloride 414 4-(2,6-dichlorobenzyloxy)-1-(6-methoxy-naphthalen-2-yl)-2-(4-methyl piperazin-1-ylmethyl)-cyclohexanol; bis-hydrochloride 415 4-(2,6-difluorobenzyloxy)-1-(6-methoxy-naphthalen-2-yl)-2-(4-methyl piperazin-1-ylmethyl)-cyclohexanol; bis-hydrochloride 416 4-(2-chloro-6-fluorobenzyloxy)-1-(6-methoxy-naphthalen-2-yl)-2-(4 methyl-piperazin-1-ylmethyl)-cyclohexanol; bis-hydrochloride 417 2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-1-naphthalen-2-yl cyclohexanol 418 4-fluoro-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(6 methoxy-naphthalen-2-yl)-cyclohexylester 419 4-fluoro-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4 naphthalen-2-yl-cyclohexylester 420 2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-1-(6-methoxy naphthalen-2-yl)-cyclohexanol 421 6-[2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-1-hydroxy cyclohexyl)-naphthalen-2-ol 

What is claimed is:
 1. A compound of formula I,

wherein A is H; or singly or multiply substituted or unsubstituted aryl or heteroaryl; R¹ is saturated or unsaturated, branched or unbranched, C₁₋₁₀ alkyl or C₃₋₁₀ cycloalkyl; aryl; heteroaryl; aryl bound by C₁₋₃ alkyl or C₁₋₃ alkylene or C₁₋₃ ethinyl; C₃₋₁₀ cycloalkyl bound by C₁₋₃ alkyl or C₁₋₃ alkylene or C₁₋₃ ethinyl; or heteroaryl bound by C₁₋₃ alkyl or C₁₋₃ alkylene or C₁₋₃ ethinyl, wherein R¹ is unsubstituted, or singly or independently multiply substituted by: F, Cl, Br, I, OR¹⁸, SR¹⁸, SO₂R¹⁸, SO₂OR¹⁸, CN, COOR¹⁸, NR¹⁹R²⁰; unsubstituted or singly or multiply substituted C₁₋₁₀ alkyl, C₃₋₁₀ cycloalkyl or silyl; unsubstituted or singly or multiply substituted aryl or heteroaryl; and unsubstituted or singly or multiply substituted aryl bound by saturated or unsaturated C₁₋₃ alkyl, C₁₋₃ alkylene, C₃₋₁₀ cycloalkyl or heteroaryl;  wherein R¹⁸ is H; saturated or unsaturated, branched or unbranched, unsubstituted or singly or multiply substituted C₁₋₁₀ alkyl or C₃₋₁₀ cycloalkyl; unsubstituted or singly or multiply substituted aryl or heteroaryl; or unsubstituted or singly or multiply substituted aryl, C₃₋₁₀ cycloalkyl or heteroaryl bound by C1-3 alkyl, C1-3 alkylene; and R¹⁹ and R²⁰ independently of one another are H; saturated or unsaturated, branched or unbranched, unsubstituted or singly or multiply substituted C₁₋₁₀ alkyl or C₃₋₁₀ cycloalkyl; unsubstituted or singly or multiply substituted aryl or heteroaryl; or unsubstituted or singly or multiply substituted aryl bound by C1-3 alkyl, C1-3 alkylene, C₃₋₁₀ cycloalkyl or heteroaryl; or R¹⁹ and R²⁰ together form CH₂CH₂OCH₂CH₂, CH₂CH₂NR²¹CH₂CH₂ or (CH₂)₃₋₆, wherein R²¹ is H; unsubstituted or substituted phenyl; or saturated or unsaturated, branched or unbranched, unsubstituted or singly or multiply substituted C₁₋₁₀ alkyl; R² and R³ independently of one another are H; saturated or unsaturated, branched or unbranched, singly or multiply substituted or unsubstituted C₁₋₁₀ alkyl or C₃₋₁₀ cycloalkyl; singly or multiply substituted or unsubstituted aryl or heteroaryl; or singly or multiply substituted or unsubstituted aryl bound by C₁₋₃ alkyl, C₁₋₃ alkylene, C₃₋₁₀ cycloalkyl or heteroaryl; or R² and R³ together represent CH₂CH₂OCH₂CH₂, CH₂CH₂NR⁶CH₂CH₂ or (CH₂)₃₋₆, wherein R⁶ is H; saturated or unsaturated, branched or unbranched, singly or multiply substituted or unsubstituted C₁₋₁₀ alkyl or C₃₋₁₀ cycloalkyl; singly or multiply substituted or unsubstituted aryl or heteroaryl; or singly or multiply substituted or unsubstituted aryl bound by C₁₋₃ alkyl, C₁₋₃ alkylene, C₃₋₁₀ cycloalkyl or heteroaryl; X has such a meaning that partial formula Ia:

partial formula Ia which is a part of formula I, is

wherein B is OH, OR⁷, H, F, Cl or NR⁸R⁹, wherein R is saturated or unsaturated, branched or unbranched, singly or multiply substituted or unsubstituted C₁₋₁₀ alkyl or C₃₋₁₀ cycloalkyl; singly or multiply substituted or unsubstituted aryl or heteroaryl; or singly or multiply substituted or unsubstituted aryl bound by C₁₋₃ alkyl, C₁₋₃ alkylene, C₃₋₁₀ cycloalkyl or heteroaryl; and R⁸ and R⁹ independently of one another are H; saturated or unsaturated, branched or unbranched, singly or multiply substituted or unsubstituted C₁₋₁₀ alkyl or C₃₋₁₀ cycloalkyl; singly or multiply substituted or unsubstituted aryl or heteroaryl; or singly or multiply substituted or unsubstituted aryl bound by C1-3 alkyl, C1-3 alkylene, C₃₋₁₀ cycloalkyl or heteroaryl; or R⁸ and R⁹ together form CH₂CH₂OCH₂CH₂, CH₂CH₂NR¹⁰CH₂CH₂ or (CH₂)₃₋₆, wherein R¹⁰ is H; saturated or unsaturated, branched or unbranched, singly or multiply substituted or unsubstituted C₁₋₁₀ alkyl or C₃₋₁₀ cycloalkyl; singly or multiply substituted or unsubstituted aryl or heteroaryl; or singly or multiply substituted or unsubstituted aryl bound by C₁₋₃ alkyl, C₁₋₃ alkylene, C₃₋₁₀ cycloalkyl or heteroaryl, and formula Ib,

formula Ib which is also part of formula I, is

wherein R⁴ is H, COR⁵, SO₂R⁵; saturated or unsaturated, branched or unbranched, singly or multiply substituted or unsubstituted C₁₋₁₀ alkyl or C₃₋₁₀ cycloalkyl; singly or multiply substituted or unsubstituted aryl or heteroaryl; or singly or multiply substituted or unsubstituted aryl bound by C₁₋₃ alkyl, C₁₋₃ alkylene, C₃₋₁₀ cycloalkyl or heteroaryl, wherein R⁵ is saturated or unsaturated, branched or unbranched, singly or multiply substituted or unsubstituted C₁₋₁₀ alkyl or C₃₋₁₀ cycloalkyl; singly or multiply substituted or unsubstituted aryl or heteroaryl; or singly or multiply substituted or unsubstituted aryl bound by C₁₋₃ alkyl. C₁₋₃ alkylene, C₃₋₁₀ cycloalkyl or heteroaryl, wherein V is OR⁴ or NR⁴R¹¹, and wherein W is R¹¹, OR¹² or NR¹¹R¹², wherein R¹¹ and R¹² independently of one another are H; saturated or unsaturated, branched or unbranched, singly or multiply substituted or unsubstituted C₇₋₁₀ alkyl or C₃₋₁₀ cycloalkyl; singly or multiply substituted or unsubstituted aryl or heteroaryl; or singly or multiply substituted or unsubstituted aryl bound by C₁₋₃ alkyl, C₁₋₃ alkylene, C₃₋₁₀ cycloalkyl or heteroaryl, wherein the compound is in the form of a racemate, a pure stereoisomer, a mixture of stereoisomers in any mixing ratio, in the illustrated form or in the form of its acid, base or a salt, or in the form of a solvate, provided that the following compounds are excluded, in which A is hydrogen, R¹ is a phenyl ring O- or S-substituted singly in the 3 position, R² and R³ are both methyl, partial formula Ia is:

wherein B is OH, and partial formula Ib is

wherein R⁴ is C₁₋₆ alkyl, C₂₋₆ alkenyl, C₅₋₇ cycloalkyl methyl, substituted or unsubstituted phenyl or substituted or unsubstituted benzyl, or in which R², R³ independently of one another are H; branched or unbranched, singly or multiply substituted or unsubstituted, saturated or unsaturated C₁-C₁₀ alkyl; saturated or unsaturated, singly or multiply substituted or unsubstituted C₃-C₇ cycloalkyl or C₃-C₇ heterocycle in which a carbon atom is replaced by N, S or O in the ring; saturated or unsaturated, singly or multiply substituted or unsubstituted alkylaryl or alkylheteroaryl; or singly or multiply substituted or unsubstituted aryl or heteroaryl; or R² and R³ together form a ring and represent CH₂CH₂OCH₂CH₂, CH₂CH₂NR⁶CH₂CH₂ or (CH₂)₃₋₆; partial formula Ia is

wherein A is hydrogen, R¹ is an unsubstituted or singly or doubly substituted phenyl ring, B is H, F, Cl, OH or OR⁷, wherein R⁷ is branched or unbranched, singly or multiply substituted or unsubstituted, saturated or unsaturated C₁-C₁₀ alkyl; singly or multiply substituted or unsubstituted saturated or unsaturated C₃-C₇ cycloalkyl or a C₃-C₇ heterocycle, in which a carbon atom is replaced in the ring by N, S or O; saturated or unsaturated, singly or multiply substituted or unsubstituted alkylaryl or alkylheteroaryl; or singly or multiply substituted or unsubstituted aryl or heteroaryl; and partial formula Ib is

wherein V is OR⁴ wherein R⁴ is COR⁵ and wherein R⁵ is unsubstituted or singly or multiply substituted C₁₋₆ alkyl.
 2. A pure enantiomer or a pure diastereomer of a compound according to claim
 1. 3. A mixture of enantiomers, or a mixture of diastereomers, in any mixing ratio, of a compound according to claim
 1. 4. A physiologically acceptable salt or a hydrate of a compound according to claim
 1. 5. A compound according to claim 1, wherein R¹ is not a phenyl ring singly O- or S-substituted in the 3 position.
 6. A compound according to claim 1, wherein R¹ is saturated or unsaturated, branched or unbranched, singly or multiply substituted or unsubstituted C₁₋₁₀ alkyl or C₃₋₁₀ cycloalkyl; naphthyl, heteroaryl, aryl bound by C₁₋₃ alkyl, C₁₋₃ alkylene or C₁₋₃ ethinyl; or C₃₋₁₀ cycloalkyl, bound by C₁₋₃ alkyl, C₁₋₃ alkylene or C₁₋₃ ethinyl, or heteroaryl bound by C₁₋₃ alkyl, or C₁₋₃ alkylene or C₁₋₃ ethinyl, wherein substitution on R¹ is by one or more radicals the group consisting of F, Cl, Br, I, OR¹⁸, SR¹⁸, SO₂R¹⁸, SO₂OR¹⁸, CN, COOR¹⁸, NR¹⁹R²⁰; unsubstituted or singly or multiply substituted C₁₋₁₀ alkyl, C₃₋₁₀ cycloalkyl; unsubstituted or singly or multiply substituted aryl or heteroaryl; and unsubstituted or singly or multiply substituted aryl bound by C₁₋₃ alkyl or C₁₋₃ alkylene, C₃₋₁₀ cycloalkyl, or heteroaryl; or R¹ corresponds to formula II

wherein R¹³, R¹⁵ and R¹⁷ independently of one another are H, F, Cl, Br, I, OR¹⁸, SR¹⁸, SO₂R¹⁸, SO₂OR¹⁸, CN, COOR¹⁸, NR¹⁹R²⁰; saturated or unsaturated, branched or unbranched, singly or multiply substituted or unsubstituted C₁₋₁₀ alkyl, C₃₋₁₀ cycloalkyl; singly or multiply substituted or unsubstituted aryl or heteroaryl; singly or multiply substituted or unsubstituted aryl bound by C₁₋₃ alkyl, C₁₋₃ alkylene, C₁₋₃ ethinyl, C₃₋₁₀ cycloalkyl, or heteroaryl; and R¹⁴ and R¹⁶ independently of one another are H, F, Cl, Br, I, SO₂R¹⁸, SO₂OR¹⁸, CN, COOR¹⁸, NR¹⁹R²⁰; saturated or unsaturated, branched or unbranched, singly or multiply substituted or unsubstituted C₁₋₁₀ alkyl, C₃₋₁₀ cycloalkyl; singly or multiply substituted or unsubstituted aryl or heteroaryl; singly or multiply substituted or unsubstituted aryl bound by C₁₋₃ alkyl, C₁₋₃ alkylene, C₁₋₃ ethinyl, C₁₋₁₀ cycloalkyl, or heteroaryl; R¹³ and R¹⁴ together form OCH₂O, OCH₂CH₂O, CH═CHO, CH═C(CH₃)O or CH═CHNH, and R¹⁵—R¹⁷ have the meaning given above, or R¹⁴ and R¹⁵ together form OCH₂O, OCH₂CH₂O, CH═CHO, CH═C(CH₃)O or CH═CHNH, and R¹³, R¹⁶ and R¹⁷ have the meaning given above, wherein R¹⁸ is H, saturated or unsaturated, branched or unbranched, unsubstituted or singly or multiply substituted C₁₋₁₀ alkyl or C₃₋₁₀ cycloalkyl; unsubstituted or singly or multiply substituted aryl or heteroaryl; or aryl bound by C₁₋₃ alkyl, C₁₋₃ alkylene, unsubstituted or singly or multiply substituted C₃₋₁₀ cycloalkyl, or heteroaryl; and R¹⁹ and R²⁰ independently of one another are H, saturated or unsaturated, branched or unbranched, unsubstituted or singly or multiply substituted C₁₋₁₀ alkyl or C₃₋₁₀ cycloalkyl; unsubstituted or singly or multiply substituted aryl or heteroaryl; or unsubstituted or singly or multiply substituted aryl bound by C1-3 alkyl or C₁₋₃ alkylene, C₃₋₁₀ cycloalkyl, or heteroaryl; or R¹⁹ and R²⁰ together form CH₂CH₂OCH₂CH₂, CH₂CH₂NR²¹CH₂CH₂ or (CH₂)₃₋₆, wherein R²¹ is H, saturated or unsaturated, branched or unbranched, unsubstituted or singly or multiply substituted C₁₋₁₀ alkyl.
 7. A compound according to claim 6, wherein R¹ is C₁₋₆ alkyl, C₃₋₆ cycloalkyl; or a heteroaryl or aryl bound by C₃₋₆ cycloalkyl.
 8. A compound according to claim 6, wherein substitution on R¹ is by one or more of C₁₋₆ alkyl, C₃₋₆ cycloalkyl, silyl, and aryl bound by C₃₋₆ cycloalkyl.
 9. A compound according to claim 6, wherein R¹³, R¹⁵ and R¹⁷ independently of one another are C₁₋₆ alkyl, C₃₋₆ cycloalkyl, silyl, or aryl bound by C₃₋₆ cycloalkyl.
 10. A compound according to claim 6, wherein R¹⁴ and R¹⁶ independently of one another are C₁₋₆ alkyl, C₃₋₆ cycloalkyl, silyl, or aryl bound by C₃₋₆ cycloalkyl.
 11. A compound according to claim 6, wherein R¹⁹ and R²⁰ are C₁₋₆ alkyl, C₃₋₆ cycloalkyl, silyl, or aryl bound by C₃₋₆ cycloalkyl.
 12. A compound according to claim 6, wherein R²¹ is C₁₋₆ alkyl.
 13. A compound according to claim 1, wherein R¹ is saturated or unsaturated, branched or unbranched, singly or multiply substituted or unsubstituted C₁₋₁₀ alkyl or C₃₋₁₀ cycloalkyl; unsubstituted or singly or multiply substituted naphthyl, heteroaryl, C₃₋₁₀ cycloalkyl, bound by C₁₋₃ alkyl, C₁₋₃ alkylene, C₁₋₃ ethinyl, and wherein substitution on R¹ is by one ore more of F, Cl, Br, I, OR¹⁸, SR¹⁸, SO₂R¹⁸, SO₂OR¹⁸, CN, COOR¹⁸, NR¹⁹R²⁰; unsubstituted or singly or multiply substituted C₁₋₁₀ alkyl, C₁₋₁₀ cycloalkyl; unsubstituted or singly or multiply substituted aryl or heteroaryl; or unsubstituted or singly or multiply substituted aryl bound by C₁₋₃ alkyl, C₁₋₃ alkylene, C₃₋₁₀ cycloalkyl, or heteroaryl.
 14. A compound according to claim 13, wherein substitution on R¹ is by one or more of C₁₋₆ alkyl, C₃₋₆ cycloalkyl, silyl, and aryl bound by C₃₋₆ cycloalkyl.
 15. A compound according to claim 6, wherein R¹ corresponds formula II, wherein R¹³, R¹⁵ and R¹⁷ independently of one another are H, F, Cl, Br, I, OR¹⁸, SR¹⁸, SO₂R¹⁸, SO₂R¹⁸, CN, COOR¹⁸, NR¹⁹R²⁰; saturated or unsaturated, branched or unbranched, singly or multiply substituted or unsubstituted C₁₋₁₀ alkyl, C₃₋₁₀ cycloalkyl; singly or multiply substituted or unsubstituted aryl or heteroaryl; singly or multiply substituted or unsubstituted aryl bound by C₁₋₃ alkyl, C₁₋₃ alkylene, C₁₋₃ ethinyl, C₃₋₁₀ cycloalkyl, or heteroaryl; wherein R¹⁴ and R¹⁶ independently of one another are H, F, Cl, Br, I, SO₂R¹⁸, SO₂OR¹⁸, CN, COOR¹⁸, NR¹⁹R²⁰; saturated or unsaturated, branched or unbranched, singly or multiply substituted or unsubstituted C₁₋₁₀ alkyl, C₃₋₁₀ cycloalkyl; singly or multiply substituted or unsubstituted aryl or heteroaryl; singly or multiply substituted or unsubstituted aryl bound by C₁₋₃ alkyl, C₁₋₃ alkylene, C₁₋₃ ethinyl, C₃₋₁₀ cycloalkyl, C₃₋₆ cycloalkyl or heteroaryl; or R¹³ and R¹⁴ together form OCH₂O, OCH₂CH₂O, CH═CHO, CH═C(CH₃)O or CH═CHNH and R¹⁵—R¹⁷ have the meaning given above, or R¹⁴ and R¹⁵ together form OCH₂O, OCH₂CH₂O, CH═CHO, CH═C(CH₃)O or CH═CHNH and R¹³, R¹⁶ and R¹⁷ have the meaning given above, wherein R¹⁸ is H; saturated or unsaturated, branched or unbranched, unsubstituted or singly or multiply substituted C₁₋₁₀ alkyl or C₃₋₁₀ cycloalkyl; unsubstituted or singly or multiply substituted aryl or heteroaryl; or unsubstituted or singly or multiply substituted aryl bound by C₁₋₃ alkyl or C₁₋₃ alkylene, C₃₋₁₀ cycloalkyl, or heteroaryl; wherein R¹⁹ and R²⁰ independently of one another are H, saturated or unsaturated, branched or unbranched, unsubstituted or singly or multiply substituted C₁₋₁₀ alkyl or C₃₋₁₀ cycloalkyl; unsubstituted or singly or multiply substituted aryl or heteroaryl; or unsubstituted or singly or multiply substituted aryl bound by C₁₋₃ alkyl, or C₁₋₃ alkylene, C₃₋₁₀ cycloalkyl, or heteroaryl; or R¹⁹ and R²⁰ together form CH₂CH₂OCH₂CH₂, CH₂CH₂NR²¹CH₂CH₂ or (CH₂)₃₋₆, wherein R²¹ is H, C₁₋₁₀ alkyl, and wherein formula Ib is

wherein R⁴ is H, COR^(5a), SO₂R⁵; saturated or unsaturated, branched or unbranched, singly or multiply substituted or unsubstituted C₁₋₁₀ alkyl or C₃₋₁₀ cycloalkyl; singly or multiply substituted or unsubstituted aryl or heteroaryl; or singly or multiply substituted or unsubstituted aryl bound by C₁₋₃ alkyl, C₁₋₃ alkylene, C₃₋₁₀ cycloalkyl or heteroaryl, wherein R⁵ is saturated or unsaturated, branched or unbranched, singly or multiply substituted or unsubstituted C₁₋₁₀ alkyl or C₃₋₁₀ cycloalkyl; singly or multiply substituted or unsubstituted aryl or heteroaryl; or singly or multiply substituted or unsubstituted aryl bound by C₁₋₃ alkyl, C₁₋₃ alkylene, C₃₋₁₀ cycloalkyl or heteroaryl, wherein R^(5a) is saturated or unsaturated, branched or unbranched, singly or multiply substituted or unsubstituted C₃₋₁₀ cycloalkyl; singly or multiply substituted or unsubstituted aryl or heteroaryl; or singly or multiply substituted or unsubstituted aryl bound by C₁₋₃ alkyl, C₁₋₃ alkylene, C₃₋₁₀ cycloalkyl or heteroaryl, wherein V is OR⁴ or NR⁴R¹¹, and wherein W is R¹¹, OR¹² or NR¹¹R¹², wherein R¹¹ and R¹² independently of one another are H; saturated or unsaturated, branched or unbranched, singly or multiply substituted or unsubstituted C₇₋₁₀ alkyl or C₃₋₁₀ cycloalkyl; singly or multiply substituted or unsubstituted aryl or heteroaryl; or singly or multiply substituted or unsubstituted aryl bound by C₁₋₃ alkyl, C₁₋₃ alkylene, C₃₋₁₀ cycloalkyl or heteroaryl.
 16. A compound according to claim 15, wherein R¹⁸ is C₁₋₆ alkyl or C₃₋₆ cycloalkyl.
 17. A compound according to claim 15, wherein R¹⁹ and R²⁰ independently of one another are C₁₋₆ alkyl, C₃₋₆ cycloalkyl, or unsubstituted or singly or multiply substituted aryl bound by C₃₋₆ cycloalkyl.
 18. A compound according to claim 15, wherein R²¹ is H, saturated or unsaturated, branched or unbranched, unsubstituted or singly or multiply substituted C₁₋₆ alkyl.
 19. A compound according to claim 1, wherein partial formula Ia is

wherein B is OH, OR⁷, H, F, Cl or NR⁸R⁹, wherein R⁷ is saturated or unsaturated, branched or unbranched singly or multiply substituted or unsubstituted C₁₋₁₀ alkyl or C₃₋₁₀ cycloalkyl, singly or multiply substituted or unsubstituted aryl or heteroaryl, or singly or multiply substituted or unsubstituted aryl bound by C₁₋₃ alkyl, C₁₋₃ alkylene, C₃₋₁₀ cycloalkyl or heteroaryl; and R⁸ and R⁹ independently of one another are H; saturated or unsaturated, branched or unbranched, singly or multiply substituted or unsubstituted C₁₋₁₀ alkyl or C₃₋₁₀ cycloalkyl; singly or multiply substituted or unsubstituted aryl or heteroaryl; or singly or multiply substituted or unsubstituted aryl bound by C₁₋₃ alkyl or C₁₋₃ alkylene, C₃₋₁₀ cycloalkyl or heteroaryl; or R⁸ and R⁹ together form CH₂CH₂OCH₂CH₂, CH₂CH₂NR¹⁰CH₂CH₂ or (CH₂)₃₋₆, wherein R¹⁰ is H; saturated or unsaturated, branched or unbranched singly or multiply substituted or unsubstituted C₁₋₁₀ alkyl or C₃₋₁₀ cycloalkyl; singly or multiply substituted or unsubstituted aryl or heteroaryl; or singly or multiply substituted or unsubstituted aryl bound by C₁₋₃ alkyl, C₁₋₃ alkylene, C₃₋₁₀ cycloalkyl or heteroaryl.
 20. A compound according to claim 1, wherein A is singly or multiply substituted or unsubstituted aryl or heteroaryl.
 21. A compound according to claim 1, wherein A is hydrogen.
 22. A compound according to claim 1, wherein R² and R³ independently of one another are H; saturated or unsaturated, branched or unbranched, singly or multiply substituted or unsubstituted C₁₋₆ alkyl or C₃₋₆ cycloalkyl; singly or multiply substituted or unsubstituted aryl or heteroaryl; or singly or multiply substituted or unsubstituted aryl bound by C₁₋₃ alkyl, C₁₋₃ alkylene, C₃₋₆ cycloalkyl or heteroaryl, or R² and R³ together form CH₂CH₂OCH₂CH₂, CH₂CH₂NR CH₂CH₂ or (CH₂)₃₋₆, wherein R⁶ is H; saturated or unsaturated, branched or unbranched, singly or multiply substituted or unsubstituted C₁₋₆ alkyl, or C₃₋₆ cycloalkyl; singly or multiply substituted or unsubstituted aryl or heteroaryl; or singly or multiply substituted or unsubstituted aryl bound by C₁₋₃ alkyl, C₁₋₃ alkylene, C₃₋₆ cycloalkyl or heteroaryl.
 23. A compound according to claim 1, wherein R⁶ is CH₃.
 24. A compound according to claim 1, wherein R⁷ is saturated or unsaturated, branched or unbranched singly or multiply substituted or unsubstituted C₁₋₆ alkyl, or C₃₋₆ cycloalkyl; singly or multiply substituted or unsubstituted aryl or heteroaryl; or singly or multiply substituted or unsubstituted aryl bound by C1-3 alkyl, C1-3 alkylene, C₃₋₆ cycloalkyl or heteroaryl.
 25. A compound according to claim 1, wherein R⁸ and R⁹ independently of one another are H; saturated or unsaturated, branched or unbranched, singly or multiply substituted or unsubstituted C₁₋₆ alkyl or C₃₋₆ cycloalkyl; singly or multiply substituted or unsubstituted aryl or heteroaryl; or singly or multiply substituted or unsubstituted aryl bound by C₁₋₃ alkyl, C₁₋₃ alkylene, C₃₋₆ cycloalkyl or heteroaryl; or R² and R³ together form CH₂CH₂OCH₂CH₂, CH₂CH₂NR¹⁰CH₂CH₂ or (CH₂)₃₋₆, wherein R¹⁰ is H; saturated or unsaturated, branched or unbranched singly or multiply substituted or unsubstituted C₁₋₆ alkyl or C₃₋₆ cycloalkyl; singly or multiply substituted or unsubstituted aryl or heteroaryl; or singly or multiply substituted or unsubstituted aryl bound by C₁₋₃ alkyl, C₁₋₃ alkylene, C₃₋₆ cycloalkyl or heteroaryl.
 26. A compound according to claim 1, wherein R⁴ is H, COR⁵, SO₂R⁵; saturated or unsaturated, branched or unbranched singly or multiply substituted or unsubstituted C₁₋₆ alkyl or C₃₋₆ cycloalkyl; singly or multiply substituted or unsubstituted aryl or heteroaryl; or singly or multiply substituted or unsubstituted aryl bound by C₁₋₃ alkyl, C₁₋₃ alkylene, C₃₋₆ cycloalkyl or heteroaryl, wherein R⁵ is singly or multiply substituted or unsubstituted C₁₋₆ alkyl; singly or multiply substituted or unsubstituted aryl or heteroaryl; or singly or multiply substituted or unsubstituted aryl bound by C₁₋₃ alkyl, C₁₋₃ alkylene, or heteroaryl.
 27. A compound according to claim 1, wherein R¹¹ and R¹² independently of one another are H; saturated or unsaturated, branched or unbranched singly or multiply substituted or unsubstituted C₁₋₆ alkyl or C₃₋₆ cycloalkyl; singly or multiply substituted or unsubstituted aryl or heteroaryl; or singly or multiply substituted or unsubstituted aryl bound by C₁₋₃ alkyl, C₁₋₃ alkylene, C₃₋₆ cycloalkyl or heteroaryl.
 28. A compound according to claim 1, wherein R¹³, R¹⁵ and R¹⁷ independently of one another are H, F, Cl, Br, I, OR¹⁸, SR¹⁸, SO₂R¹⁸, SO₂OR¹⁸, CN, COOR¹⁸, NR¹⁹R²⁰; saturated or unsaturated, branched or unbranched, singly or multiply substituted or unsubstituted C₁₋₆ alkyl, C₃₋₆ cycloalkyl or silyl; singly or multiply substituted or unsubstituted aryl or heteroaryl; singly or multiply substituted or unsubstituted aryl bound by C₁₋₃ alkyl, C₁₋₃ alkylene, C₁₋₃ ethinyl, C₃₋₆ cycloalkyl or heteroaryl.
 29. A compound according to claim 1, wherein R¹⁴ and R¹⁶ independently of one another are H, F, Cl, Br, I, SO₂R¹⁸, SO₂OR¹⁸, CN, COOR¹⁸, NR¹⁹R²⁰; saturated or unsaturated, branched or unbranched, singly or multiply substituted or unsubstituted C₁₋₆ alkyl, C₃₋₆ cycloalkyl or silyl; singly or multiply substituted or unsubstituted aryl or heteroaryl; singly or multiply substituted or unsubstituted aryl bound by C₁₋₃ alkyl, C₁₋₃ alkylene, C₁₋₃ ethinyl, C₃₋₆ cycloalkyl or heteroaryl; or R¹³ and R¹⁴ together form the group OCH₂O, OCH₂CH₂O, CH═CHO, CH═C(CH₃)O or CH═CHNH, or R¹⁴ and R¹⁵ together form the group OCH₂O, OCH₂CH₂O, CH═CHO, CH═C(CH₃)O or CH═CHNH and R¹³.
 30. A compound according to claim 1, wherein R¹⁸ is saturated or unsaturated, branched or unbranched, unsubstituted or singly or multiply substituted C₁₋₆ alkyl or C₃₋₆ cycloalkyl; unsubstituted or singly or multiply substituted aryl or heteroaryl; or unsubstituted or singly or multiply substituted aryl bound by C₁₋₃ alkyl, C₁₋₃ alkylene, C₁₋₃ ethinyl, C₃₋₆ cycloalkyl or heteroaryl.
 31. A compound according to claim 1, wherein R¹⁹ and R²⁰ independently of one another are H; saturated or unsaturated, branched or unbranched, unsubstituted or singly or multiply substituted C₁₋₆ alkyl or C₃₋₆ cycloalkyl; unsubstituted or singly or multiply substituted aryl or heteroaryl; or unsubstituted or singly or multiply substituted aryl bound by C₁₋₃ alkyl, C₁₋₃ alkylene, C₃₋₆ cycloalkyl or heteroaryl; or R¹⁹ and R²⁰ together form CH₂CH₂OCH₂CH₂, CH₂CH₂NR¹⁰CH₂CH₂ or (CH₂)₃₋₆.
 32. A compound according to claim 1, wherein R²¹ is H, or saturated or unsaturated, branched or unbranched, unsubstituted or singly or multiply substituted C₁₋₆ alkyl.
 33. A compound according to claim 1, wherein R² and R³ independently of one another are H; saturated or unsaturated, branched or unbranched, singly or multiply substituted or unsubstituted C₁₋₆ alkyl or C₃₋₆ cycloalkyl; singly or multiply substituted or unsubstituted aryl or heteroaryl; or singly or multiply substituted or unsubstituted aryl bound by C₁₋₃ alkyl, C₁₋₃ alkylene, C₃₋₆ cycloalkyl or heteroaryl, or R² and R³ together form CH₂CH₂OCH₂CH₂, CH₂CH₂NR⁶CH₂CH₂ or (CH₂)₃₋₆, wherein R⁶ is H; saturated or unsaturated, branched or unbranched, singly or multiply substituted or unsubstituted C₁₋₆ alkyl, or C₃₋₆ cycloalkyl; singly or multiply substituted or unsubstituted aryl or heteroaryl; or singly or multiply substituted or unsubstituted aryl bound by C₁₋₃ alkyl, C₁₋₃ alkylene, C₃₋₆ cycloalkyl or heteroaryl; and R⁷ is saturated or unsaturated, branched or unbranched singly or multiply substituted or unsubstituted C₁₋₆ alkyl, or C₃₋₆ cycloalkyl; singly or multiply substituted or unsubstituted aryl or heteroaryl; or singly or multiply substituted or unsubstituted aryl bound by C1-3 alkyl, C₁₋₃ alkylene, C₃₋₆ cycloalkyl or heteroaryl; and R⁸ and R⁹ independently of one another are H; saturated or unsaturated, branched or unbranched, singly or multiply substituted or unsubstituted C₁₋₆ alkyl or C₃₋₆ cycloalkyl; singly or multiply substituted or unsubstituted aryl or heteroaryl; or singly or multiply substituted or unsubstituted aryl bound by C₁₋₃ alkyl, C₁₋₃ alkylene, C₃₋₆ cycloalkyl or heteroaryl; or R² and R³ together form CH₂CH₂OCH₂CH₂, CH₂CH₂NR¹⁰CH₂CH₂ or (CH₂)₃₋₆, wherein R¹⁰ is H; saturated or unsaturated, branched or unbranched singly or multiply substituted or unsubstituted C₁₋₆ alkyl or C₃₋₆ cycloalkyl; singly or multiply substituted or unsubstituted aryl or heteroaryl; or singly or multiply substituted or unsubstituted aryl bound by C₁₋₃ alkyl, C₁₋₃ alkylene, C₃₋₆ cycloalkyl or heteroaryl, and R⁴ is H, COR⁵, SO₂R⁵; saturated or unsaturated, branched or unbranched singly or multiply substituted or unsubstituted C₁₋₆ alkyl or C₃₋₆ cycloalkyl; singly or multiply substituted or unsubstituted aryl or heteroaryl; or singly or multiply substituted or unsubstituted aryl bound by C₁₋₃ alkyl, C₁₋₃ alkylene, C₃₋₆ cycloalkyl or heteroaryl, wherein R⁵ is singly or multiply substituted or unsubstituted C₁₋₆ alkyl; singly or multiply substituted or unsubstituted aryl or heteroaryl; or singly or multiply substituted or unsubstituted aryl bound by C₁₋₃ alkyl, C₁₋₃ alkylene, or heteroaryl, and R¹¹ and R¹² independently of one another are H; saturated or unsaturated, branched or unbranched singly or multiply substituted or unsubstituted C₁₋₆ alkyl or C₃₋₆ cycloalkyl; singly or multiply substituted or unsubstituted aryl or heteroaryl; or singly or multiply substituted or unsubstituted aryl bound by C₁₋₃ alkyl, C₁₋₃ alkylene, C₃₋₆ cycloalkyl or heteroaryl; and R¹³, R¹⁵ and R¹⁷ independently of one another are H, F, Cl, Br, I, OR¹⁸, SR¹⁸, SO₂R¹⁸, SO₂OR¹⁸, CN, COOR¹⁸, NR¹⁹R²⁰; saturated or unsaturated, branched or unbranched, singly or multiply substituted or unsubstituted C₁₋₆ alkyl, C₃₋₆ cycloalkyl or silyl; singly or multiply substituted or unsubstituted aryl or heteroaryl; singly or multiply substituted or unsubstituted aryl bound by C₁₋₃ alkyl, C₁₋₃ alkylene, C₁₋₃ ethinyl, C₃₋₆ cycloalkyl or heteroaryl; and R¹⁴ and R¹⁶ independently of one another are H, F, Cl, Br, I, SO₂R¹⁸, SO₂OR¹⁸, CN, COOR¹⁸, NR¹⁹R²⁰; saturated or unsaturated, branched or unbranched, singly or multiply substituted or unsubstituted C₁₋₆ alkyl, C₃₋₆ cycloalkyl or silyl; singly or multiply substituted or unsubstituted aryl or heteroaryl; singly or multiply substituted or unsubstituted aryl bound by C₁₋₃ alkyl, C₁₋₃ alkylene, C₁₋₃ ethinyl, C₃₋₆ cycloalkyl or heteroaryl; or R¹³ and R¹⁴ together form the group OCH₂O, OCH₂CH₂O, CH═CHO, CH═C(CH₃)O or CH═CHNH, or R¹⁴ and R¹⁵ together form the group OCH₂O, OCH₂CH₂O, CH═CHO, CH═C(CH₃)O or CH═CHNH and R¹³, and R¹⁸ is saturated or unsaturated, branched or unbranched, unsubstituted or singly or multiply substituted C₁₋₆ alkyl or C₃₋₆ cycloalkyl; unsubstituted or singly or multiply substituted aryl or heteroaryl; or unsubstituted or singly or multiply substituted aryl bound by C₁₋₃ alkyl, C₁₋₃ alkylene, C₁₋₃ ethinyl, C₃₋₆ cycloalkyl or heteroaryl; and R¹⁹ and R²⁰ independently of one another are H; saturated or unsaturated, branched or unbranched, unsubstituted or singly or multiply substituted C₁₋₆ alkyl or C₃₋₆ cycloalkyl; unsubstituted or singly or multiply substituted aryl or heteroaryl; or unsubstituted or singly or multiply substituted aryl bound by C₁₋₃ alkyl, C₁₋₃ alkylene, C₃₋₆ cycloalkyl or heteroaryl; or R¹⁹ and R²⁰ together form CH₂CH₂OCH₂CH₂, CH₂CH₂NR¹⁰CH₂CH₂ or (CH₂)₃₋₆, and R²¹ is H, or saturated or unsaturated, branched or unbranched, unsubstituted or singly or multiply substituted C₁₋₆ alkyl.
 34. A compound of claim 1, wherein A is hydrogen, or unsubstituted or singly or multiply substituted phenyl.
 35. A compound of claim 1, wherein A is hydrogen.
 36. A compound of claim 1, wherein R² and R³ are independently of each other saturated or unsaturated, branched or unbranched, unsubstituted or singly or multiply substituted C₁₋₆ alkyl, or R² and R³ together represent CH₂CH₂NR¹⁰CH₂CH₂ or (CH₂)₃₋₆, and wherein R⁶ is H or saturated, branched or unbranched, and unsubstituted C₁₋₆ alkyl.
 37. A compound according to claim 36, wherein at least one of R² and R³ is CH₃.
 38. A compound according to claim 37, wherein both R² and R³ are CH₃.
 39. A compound according to claim 36, wherein R⁶ is H or CH₃.
 40. A compound according to claim 1, wherein R¹ is saturated or unsaturated, branched or unbranched C₁₋₆ alkyl; C₃₋₆ cycloalkyl; naphthyl; phenyl; furyl; thiophenyl; naphthyl bound by C₁₋₃ alkylene or C₁₋₃ ethinyl; phenyl, C₃₋₆ cycloalkyl or thiophenyl bound by C₁₋₃ alkyl, C₁₋₃ alkylene, C₁₋₃ ethinyl or furyl.
 41. A compound according to claim 1, wherein partial formula Ib is


42. A compound according to claim 1, wherein R¹ is naphthyl or naphthyl bound by C₁₋₃ alkyl, alkylene or C₁₋₃ ethinyl, unsubstituted or singly or multiply substituted by at least one radical selected independently of one another from the group consisting of F, Cl, Br, I, OR¹⁸, SR¹⁸, SO₂R¹⁸, SO₂OR¹⁸, CN, COOR¹⁸, NR¹⁹R²⁰; unsubstituted or singly or multiply substituted C₁₋₁₀ alkyl, C₃₋₁₀ cycloalkyl or silyl; unsubstituted or singly or multiply substituted aryl or heteroaryl; and unsubstituted or singly or multiply substituted aryl bound by C₁₋₃ alkyl, C₁₋₃ alkylene, C₃₋₁₀ cycloalkyl or heteroaryl; wherein R¹⁸ is H; saturated or unsaturated, branched or unbranched, unsubstituted or singly or multiply substituted C₁₋₁₀ alkyl or C₃₋₁₀ cycloalkyl; unsubstituted or singly or multiply substituted aryl or heteroaryl; or unsubstituted or singly or multiply substituted aryl bound by C₁₋₃ alkyl, C₁₋₃ alkylene, C₃₋₁₀ cycloalkyl or heteroaryl; R¹⁹ and R²⁰ independently of one another are H; saturated or unsaturated, branched or unbranched, unsubstituted or singly or multiply substituted C₁₋₁₀ alkyl or C₃₋₁₀ cycloalkyl; unsubstituted or singly or multiply substituted aryl or heteroaryl; or unsubstituted or singly or multiply substituted aryl bound by C₁₋₃ alkyl, C₁₋₃ alkylene, C₃₋₁₀ cycloalkyl or heteroaryl; or R¹⁹ and R²⁰ together form CH₂CH₂OCH₂CH₂, CH₂CH₂NR²¹CH₂CH₂ or (CH₂)₃₋₆, wherein R²¹ is H; saturated or unsaturated, branched or unbranched, unsubstituted or singly or multiply substituted C₁₋₁₀ alkyl; R² and R³ independently of one another are H; saturated or unsaturated, branched or unbranched singly or multiply substituted or unsubstituted C₁₋₁₀ alkyl or C₃₋₁₀ cycloalkyl; singly or multiply substituted or unsubstituted aryl or heteroaryl; or singly or multiply substituted or unsubstituted aryl bound by C₁₋₃ alkyl, C₁₋₃ alkylene, C₃₋₁₀ cycloalkyl or heteroaryl; or R² and R³ together represent CH₂CH₂OCH₂CH₂, CH₂CH₂NR⁶CH₂CH₂ or (CH₂)₃₋₆, wherein R⁶ is H; saturated or unsaturated, branched or unbranched singly or multiply substituted or unsubstituted C₁₋₁₀ alkyl or C₃₋₁₀ cycloalkyl; singly or multiply substituted or unsubstituted aryl or heteroaryl; or singly or multiply substituted or unsubstituted aryl bound by C₁₋₃ alkyl, C₁₋₃ alkylene, C₃₋₁₀ cycloalkyl or heteroaryl; partial formula Ia is

wherein B is OH, OR⁷, H, F, Cl or NR⁸R⁹, wherein R⁷ is saturated or unsaturated, branched or unbranched singly or multiply substituted or unsubstituted C₁₋₁₀ alkyl or C₃₋₁₀ cycloalkyl; singly or multiply substituted or unsubstituted aryl or heteroaryl; or singly or multiply substituted or unsubstituted aryl bound by C₁₋₃ alkyl, C₁₋₃ alkylene, C₃₋₁₀ cycloalkyl or heteroaryl; and R⁸ and R⁹ independently of one another are H; saturated or unsaturated, branched or unbranched singly or multiply substituted or unsubstituted C₁₋₁₀ alkyl or C₃₋₁₀ cycloalkyl; singly or multiply substituted or unsubstituted aryl or heteroaryl; or singly or multiply substituted or unsubstituted aryl bound by C₁₋₃ alkyl, C₁₋₃ alkylene, C₃₋₁₀ cycloalkyl or heteroaryl; or R⁸ and R⁹ together form CH₂CH₂OCH₂CH₂, CH₂CH₂NR¹⁰CH₂CH₂ or (CH₂)₃₋₆, wherein R¹⁰ is H; saturated or unsaturated, branched or unbranched singly or multiply substituted or unsubstituted C₁₋₁₀ alkyl or C₃₋₁₀ cycloalkyl; singly or multiply substituted or unsubstituted aryl or heteroaryl; or singly or multiply substituted or unsubstituted aryl bound by C₁₋₃ alkyl, C₁₋₃ alkylene, C₃₋₁₀ cycloalkyl or heteroaryl; partial formula Ib is

wherein V is OR⁴, wherein R⁴ is H, COR⁵; saturated or unsaturated, branched or unbranched singly or multiply substituted or unsubstituted C₁₋₁₀ alkyl; saturated or unsaturated, singly or multiply substituted or unsubstituted C₃₋₁₀ cycloalkyl; singly or multiply substituted or unsubstituted aryl or heteroaryl; or singly or multiply substituted or unsubstituted aryl bound by C₁₋₃ alkyl, C₃₋₁₀ cycloalkyl or heteroaryl, wherein R⁵ is saturated or unsaturated, branched or unbranched, singly or multiply substituted or unsubstituted C₁₋₁₀ alkyl; saturated or unsaturated, singly or multiply substituted or unsubstituted C₃₋₁₀ cycloalkyl; singly or multiply substituted or unsubstituted aryl or heteroaryl; or singly or multiply substituted or unsubstituted aryl bound by C₁₋₃ alkyl, C₁₋₃ alkylene, C₃₋₁₀ cycloalkyl or heteroaryl.
 43. A compound according to claim 42, wherein A is H or singly or multiply substituted or unsubstituted phenyl.
 44. A compound according to claim 43, wherein A is H.
 45. A compound according to claim 42, wherein R¹ is naphthyl, unsubstituted or substituted by OH or OCH₃.
 46. A compound according to claim 42, wherein one or both of R² and R³ are CH₃, or R² and R³ together represent together represent CH₂CH₂NR⁶CH₂CH₂, wherein R⁶ is H or CH₃.
 47. A compound according to claim 42, wherein partial formula Ia is

wherein B is OH.
 48. A compound according to claim 42, wherein A is H or singly or multiply substituted or unsubstituted phenyl; and R¹ is naphthyl, unsubstituted or singly or multiply substituted by at least one radical selected independently of one another from the group consisting of F, Cl, Br, I, OR¹⁸; and branched or unbranched, unsubstituted or singly or multiply substituted C₁₋₄ alkyl; wherein R¹⁸ is H; branched or unbranched, unsubstituted or singly or multiply substituted C₁₋₄ alkyl; and R² and R³ are saturated or unsaturated, branched or unbranched, unsubstituted or singly or multiply substituted C₁₋₆ alkyl, or R² and R³ together represent CH₂CH₂NR⁶CH₂CH₂ or (CH₂)₄₋₅, wherein R⁶ is H or saturated, branched or unbranched, and unsubstituted C₁₋₆ alkyl; and partial formula Ia is

wherein B is OH, OR⁷, H, F, or Cl, wherein R⁷ is branched or unbranched, singly or multiply substituted or unsubstituted C₁₋₄ alkyl; and partial formula Ib is

wherein V is OR⁴, wherein R⁴ is COR⁵; singly or multiply substituted or unsubstituted phenyl or benzyl; in particular COR⁵ or singly or multiply substituted or unsubstituted benzyl; wherein R⁵ is saturated or unsaturated, branched or unbranched, singly or multiply substituted or unsubstituted C₁₋₁₀ alkyl, in particular C₁₋₆ alkyl; or singly or multiply substituted or unsubstituted phenyl.
 49. A compound according to claim 42, wherein A is H, R¹ is naphthyl, unsubstituted or substituted by OH or OCH₃, one or both R² and R³ are CH₃; or R² and R³ together represent CH₂CH₂NR⁶CH₂CH₂ R⁶ is H or CH₃; and partial formula Ia is

wherein B is OH.
 50. A compound according to claim 1, selected from the group consisting of 4-benzyloxy-1-(4-bromophenyl)-2-dimethylaminomethyl-cyclohexanol; 4-benzyloxy-2-dimethylaminomethyl-1-(4-trifluoromethyl-phenyl)-cyclohexanol; 4-benzyloxy-1-(3,4-difluorophenyl)-2-dimethylaminomethyl-cyclohexanol; 4-benzyloxy-2-dimethylaminomethyl-1-(3-fluoro-4-methyl-phenyl)-cyclohexanol; 4-benzyloxy-1-(3,4-dichlorophenyl)-2-dimethylaminomethyl-cyclohexanol; 4-benzyloxy-2-dimethylaminomethyl-1-naphthalen-2-yl-cyclohexanol; 4-benzyloxy-2-dimethylaminomethyl-1-(3,4-dimethyl-phenyl)-cyclohexanol; 4-benzyloxy-2-dimethylaminomethyl-1-(4-fluoro-3-methyl-phenyl)-cyclohexanol; 4-benzyloxy-2-dimethylaminomethyl-1-(5-fluoro-2-methyl-phenyl)-cyclohexanol; 4-benzyloxy-1-(3-chloro-4-fluorophenyl)-2-dimethylaminomethyl-cyclohexanol; 4-benzyloxy-1-(5-chloro-2-methoxy-phenyl)-2-dimethylaminomethyl-cyclohexanol; 4-benzyloxy-1-(2-bromophenyl)-2-dimethylaminomethyl-cyclohexanol; 4-benzyloxy-2-dimethylaminomethyl-1-(2-methoxy-phenyl)-cyclohexanol; 4-benzyloxy-2-dimethylaminomethyl-1-(2-methylsulfanyl-phenyl)-cyclohexanol; 4-benzyloxy-1-(4-chlorophenyl)-2-dimethylaminomethyl-cyclohexanol; 4-benzyloxy-1-(3-bromophenyl)-2-dimethylaminomethyl-cyclohexanol; 4-benzyloxy-1-(4-bromo-3-fluorophenyl)-2-dimethylaminomethyl-cyclohexanol; 4-benzyloxy-2-dimethylaminomethyl-1-(4-methoxy-phenyl)-cyclohexanol; 4-benzyloxy-1-(2-chlorophenyl)-2-dimethylaminomethyl-cyclohexanol; 4-benzyloxy-2-dimethylaminomethyl-1-(3-trifluoromethyl-phenyl)-cyclohexanol; 4-benzyloxy-2-dimethylaminomethyl-1-(4-pentyl-phenyl)-cyclohexanol; 4-benzyloxy-2-dimethylaminomethyl-1-(2,5-dimethyl-phenyl)-cyclohexanol; 4-benzyloxy-2-dimethylaminomethyl-1-(4-isopropyl-phenyl)-cyclohexanol; 4-benzyloxy-2-dimethylaminomethyl-1-(2,3-dimethyl-phenyl)-cyclohexanol; 4-benzyloxy-2-dimethylaminomethyl-1-(3-fluorophenyl)-cyclohexanol; 4-benzyloxy-1-(3,5-bis-trifluoromethyl-phenyl)-2-dimethylaminomethyl-cyclohexanol; 4-benzyloxy-2-dimethylaminomethyl-1-(4-ethyl-phenyl)-cyclohexanol; 4-benzyloxy-1-(3,5-dichlorophenyl)-2-dimethylaminomethyl-cyclohexanol; 2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-1-o-tolyl-cyclohexanol; 2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-1-p-tolyl-cyclohexanol; 2-dimethylaminomethyl-1-(2,5-dimethyl-phenyl)-4-(4-fluorobenzyloxy)-cyclohexanol; 2-dimethylaminomethyl-1-(3,4-dimethyl-phenyl)-4-(4-fluorobenzyloxy)-cyclohexanol; 2-dimethylaminomethyl-1-(3,5-dimethyl-phenyl)-4-(4-fluorobenzyloxy)-cyclohexanol; 2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-1-(4-isopropyl-phenyl)-cyclohexanol; 2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-1-(3-fluorophenyl)-cyclohexanol; 2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-1-(4-fluorophenyl)-cyclohexanol; 1-(3,4-difluorophenyl)-2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-cyclohexanol; 2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-1-(3-fluoro-4-methyl-phenyl)-cyclohexanol; 2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-1-(4-fluoro-3-methyl-phenyl)-cyclohexanol; 1-(2-chlorophenyl)-2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-cyclohexanol; 1-(3-chlorophenyl)-2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-cyclohexanol; 1-(4-chlorophenyl)-2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-cyclohexanol; 1-(3,4-dichlorophenyl)-2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-cyclohexanol; 1-(4-chloro-3-fluorophenyl)-2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-cyclohexanol; 1-(3,5-dichlorophenyl)-2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-cyclohexanol; 1-(4-chloro-2-methoxy-phenyl)-2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-cyclohexanol; 2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-1-(4-trifluoromethyl-phenyl)-cyclohexanol; 1-(3,5-bis-trifluoromethyl-phenyl)-2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-cyclohexanol; 2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-1-(2-methoxy-phenyl)-cyclohexanol; 2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-1-(2-methylsulfanyl-phenyl)-cyclohexanol; (5-benzyloxy-2-thiophen-2-yl-cyclohex-2-enylmethyl)-dimethyl-amine; [5-(4-fluorobenzyloxy)-2-thiophen-2-yl-cyclohex-2-enylmethyl]-dimethyl-amine; 3,4-dichloro-N-[3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexyl]-benzamide; naphthalene-2-carboxylic acid [3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy phenyl)-cyclohexyl]-amide; N-[3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexyl]-3-phenyl-propionamide; N-[3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexyl]-4-nitro-benzamide; N-[3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexyl]-4-methyl-3-nitro-benzamide; N-[3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexyl]-3,4,5-trimethoxy-benzamide; 2-(4-chlorophenoxy)-N-[3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexyl]-acetamide; N, [3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexyl]-3-nitro-benzamide; furan-2-carboxylic acid [3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexyl]-amide; N-[3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexyl]-2-phenoxy-acetamide; N-[3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexyl]-4-trifluoromethyl-benzamide; N-[3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexyl]-4-methoxy-benzamide; 2-dimethylaminomethyl-1-(4-fluorophenyl)-4-phenethyl-cyclohexanol; 1-(4-bromophenyl)-2-dimethylaminomethyl-4-phenethyl-cyclohexanol; 2-dimethylaminomethyl-1-(4-ethyl-phenyl)-4-phenethyl-cyclohexanol; 2-dimethylaminomethyl-1-(4-isopropyl-phenyl)-4-phenethyl-cyclohexanol; 2-dimethylaminomethyl-1-(4-methoxy-phenyl)-4-phenethyl-cyclohexanol; 2-dimethylaminomethyl-1-(2,4-dimethyl-phenyl)-4-phenethyl-cyclohexanol; 2-dimethylaminomethyl-1-(2-methylsulfanyl-phenyl)-4-phenethyl-cyclohexanol; 2-dimethylaminomethyl-1-(5-fluoro-2-methyl-phenyl)-4-phenethyl-cyclohexanol; 2-dimethylaminomethyl-1-(2,5-dimethyl-phenyl)-4-phenethyl-cyclohexanol; 2-dimethylaminomethyl-4-phenethyl-1-p-tolyl-cyclohexanol; 2-dimethylaminomethyl-1-(3-fluorophenyl)-4-phenethyl-cyclohexanol; 1-(3-chlorophenyl)-2-dimethylaminomethyl-4-phenethyl-cyclohexanol; 1-(4-chloro-3-fluorophenyl)-2-dimethylaminomethyl-4-phenethyl-cyclohexanol; 2-dimethylaminomethyl-4-phenethyl-1-(3-trifluoromethyl-phenyl)-cyclohexanol; 1-(3,5-dichlorophenyl)-2-dimethylaminomethyl-4-phenethyl-cyclohexanol; 2-dimethylaminomethyl-1-(3,4-dimethyl-phenyl)-4-phenethyl-cyclohexanol; 1-(3,4-dichlorophenyl)-2-dimethylaminomethyl-4-phenethyl-cyclohexanol; 1-(4-chlorophenyl)-2-dimethylaminomethyl-4-phenethyl-cyclohexanol; 2-dimethylaminomethyl-1-(3-fluoro-4-methyl-phenyl)-4-phenethyl-cyclohexanol; 2-dimethylaminomethyl-1-(3,5-dimethyl-phenyl)-4-phenethyl-cyclohexanol; 1-(4-bromo-3-fluorophenyl)-2-dimethylaminomethyl-4-phenethyl-cyclohexanol; 1-(3,4-difluorophenyl)-2-dimethylaminomethyl-4-phenethyl-cyclohexanol; 2-dimethylaminomethyl-1-(2,3-dimethyl-phenyl)-4-phenethyl-cyclohexanol; 2-dimethylaminomethyl-1-naphthalen-1-yl-4-phenethyl-cyclohexanol; 1-(3,5-bis-trifluoromethyl-phenyl)-2-dimethylaminomethyl-4-phenethyl-cyclohexanol; 1-(3-bromophenyl)-2-dimethylaminomethyl-4-phenethyl-cyclohexanol; 2-dimethylaminomethyl-1-(4-fluoro-3-methyl-phenyl)-4-phenethyl-cyclohexanol; 2-dimethylaminomethyl-4-phenethyl-1-m-tolyl-cyclohexanol; 4-benzyl-2-dimethylaminomethyl-1-m-tolyl-cyclohexanol; 4-benzyl-1-(3,4-difluorophenyl)-2-dimethylaminomethyl-cyclohexanol; 4-benzyl-2-dimethylaminomethyl-1-p-tolyl-cyclohexanol; 2-dimethylaminomethyl-4-(3-methoxy-benzyl)-1-p-tolyl-cyclohexanol; 1-(4-chlorophenyl)-2-dimethylaminomethyl-4-(3-methoxy-benzyl)-cyclohexanol; 1-(4-bromo-3-fluorophenyl)-2-dimethylaminomethyl-4-(3-methoxy-benzyl)-cyclohexanol; 2-dimethylaminomethyl-4-(4-fluorobenzyl)-1-p-tolyl-cyclohexanol; 1-(4-chlorophenyl)-2-dimethylaminomethyl-4-(4-fluorobenzyl)-cyclohexanol; dimethyl-[2-(5-methyl-thiophen-2-yl)-5-phenethyl-cyclohex-2-eny[methyl]amine; [2-(3,5-bis-trifluoromethyl-phenyl)-5-phenethyl-cyclohex-1-enylmethyl]-dimethylamine; dimethyl-(5-phenethyl-2-p-tolyl-cyclohex-1-enylmethyl)-amine; [2-(3-chloro-4-fluorophenyl)-5-phenethyl-cyclohex-1-enylmethyl]-dimethyl-amine; [2-(2,5-dimethyl-phenyl)-5-phenethyl-cyclohex-1-enylmethyl]-dimethyl-amine; dimethyl-(5-phenethyl-2-p-tolyl-cyclohex-2-enylmethyl)-amine; [2-(3,5-bis-trifluoromethyl-phenyl)-5-phenethyl-cyclohex-2-enylmethyl]-dimethylamine; [2-(3-chloro-4-fluorophenyl)-5-phenethyl-cyclohex-2-enylmethyl]-dimethyl-amine; [2-(3-chloro-4-fluorophenyl)-2-fluoro5-phenethyl-cyclohexylmethyl]-dimethylamine; [2-fluoro-5-(4-fluorobenzyl)-2-p-tolyl-cyclohexylmethyl]-dimethyl-amine; benzyl-2-(dimethylamino-phenyl-methyl)-4-phenyl-cyclohexanol; 2-(dimethylamino-phenyl-methyl)-4-phenyl-1-vinyl-cyclohexanol; 1-(4-tert-butyl-phenyl)-2-(dimethylamino-phenyl-methyl)-4-phenyl-cyclohexanol; 2-(dimethylamino-phenyl-methyl)-4-phenyl-1-m-tolyl-cyclohexanol; 2-(dimethylamino-phenyl-methyl)-1-phenethyl-4-phenyl-cyclohexanol; 2-(dimethylamino-phenyl-methyl)-4-phenyl-1-phenylethynyl-cyclohexanol; 2-(dimethylamino-phenyl-methyl)-1-(3-methoxy-phenyl)-4-phenyl-cyclohexanol; 2-(dimethylamino-phenyl-methyl)-4-phenyl-1-(3-phenyl-propyl)-cyclohexanol; 2-(dimethylamino-phenyl-methyl)-1-(4-methoxy-phenyl)-4-phenyl-cyclohexanol; 2-(dimethylamino-phenyl-methyl)-1-(2-methoxy-phenyl)-4-phenyl-cyclohexanol; 4-benzyloxy-2-dimethylaminomethyl-1-phenyl-cyclohexanol; 1-benzyl-4-benzyloxy-2-dimethylaminomethyl-cyclohexanol; 4-benzyloxy-2-dimethylaminomethyl-1-(4-fluoro-3-methyl-phenyl)-cyclohexanol; 4-benzyloxy-2-dimethylaminomethyl-1-o-tolyl-cyclohexanol; 4-benzyloxy-2-dimethylaminomethyl-1-vinyl-cyclohexanol; 4-benzyloxy-1-cyclopentyl-2-dimethylaminomethyl-cyclohexanol; 4-benzyloxy-2-dimethylaminomethyl-1-m-tolyl-cyclohexanol; 4-benzyloxy-2-dimethylaminomethyl-bicyclohexyl-1-ol; 4-benzyloxy-2-dimethylaminomethyl-1-(4-fluorophenyl)-cyclohexanol; 4-benzyloxy-2-dimethylaminomethyl-1-phenylethynyl-cyclohexanol; 4-benzyloxy-2-dimethylaminomethyl-1-thiophen-2-yl-cyclohexanol; 4-benzyloxy-2-dimethylaminomethyl-1-(3-methoxy-phenyl)-cyclohexanol; 4-benzyloxy-2-dimethylaminomethyl-1-(3-phenyl-propyl)-cyclohexanol; 4-benzyloxy-2-dimethylaminomethyl-1-p-tolyl-cyclohexanol; 4-benzyloxy-2-dimethylaminomethyl-1-(4-methoxy-phenyl)-cyclohexanol; 4-benzyloxy-2-dimethylaminomethyl-1-(3-fluorophenyl)-cyclohexanol; 4-benzyloxy-1-(3-chlorophenyl)-2-dimethylaminomethyl-cyclohexanol; 4-benzyloxy-2-dimethylaminomethyl-1-(3-methoxy-benzyl)-cyclohexanol; 4-benzyloxy-1-(4-chloro-3-trifluoromethyl-phenyl)-2-dimethylaminomethylcyclohexanol; 4-benzyloxy-2-dimethylaminomethyl-1-(3-fluorobenzyl)-cyclohexanol; 4-benzyloxy-2-dimethylaminomethyl-1-(2-methyl-benzyl)-cyclohexanol; 4-benzyloxy-2-dimethylaminomethyl-1-(2,5-dimethyl-benzyl)-cyclohexanol; 4-(4-chlorobenzyl)-2-dimethylaminomethyl-1-(3-methoxy-phenyl)-cyclohexanol; 4-(4-chlorobenzyl)-2-dimethylaminomethyl-1-(3-phenyl-propyl)-cyclohexanol; 4-(4-chlorobenzyl)-1-(2,3-dichlorophenyl)-2-dimethylaminomethyl-cyclohexanol; 4-(4-chlorobenzyl)-1-cyclohexylmethyl-2-dimethylaminomethyl-cyclohexanol; 4-(4-chlorobenzyl)-2-dimethylaminomethyl-1-(5-fluoro-2-methoxy-phenyl)-cyclohexanol; 4-(4-chlorobenzyl)-2-dimethylaminomethyl-1-(3-fluorophenyl)-cyclohexanol; 4-(4-chlorobenzyl)-1-(3-chlorophenyl)-2-dimethylaminomethyl-cyclohexanol; 4-(4-chlorobenzyl)-1-(3,5-dichlorophenyl)-2-dimethylaminomethyl-cyclohexanol; 4-(4-chlorobenzyl)-1-(2-chlorobenzyl)-2-dimethylaminomethyl-cyclohexanol; 4-(4-chlorobenzyl)-2-dimethylaminomethyl-1-(4-fluorobenzyl)-cyclohexanol; 4-(4-chlorobenzyl)-2-dimethylaminomethyl-1-(3-fluorobenzyl)-cyclohexanol; 4-(4-chlorobenzyl)-2-dimethylaminomethyl-1-(2-methoxy-phenyl)-cyclohexanol; 4-(4-chlorobenzyl)-2-dimethylaminomethyl-1-(2-methyl-benzyl)-cyclohexanol; 4-(4-chlorobenzyl)-2-dimethylaminomethyl-1-(3-methyl-benzyl)-cyclohexanol; 1,4-bis-(4-chlorobenzyl)-2-dimethylaminomethyl-cyclohexanol; 4-(4-chlorobenzyl)-1-(2-chloro-6-fluorobenzyl)-2-dimethylaminomethyl-cyclohexanol; 4-(4-chlorobenzyl)-2-dimethylaminomethyl-1-(2,5-dimethyl-benzyl)-cyclohexanol; 4-(4-chlorobenzyl)-1-(3-chlorobenzyl)-2-dimethylaminomethyl-cyclohexanol; 4-(4-chlorobenzyl)-1-(2,4-dichlorobenzyl)-2-dimethylaminomethyl-cyclohexanol; 4-(4-chlorobenzyl)-2-dimethylaminomethyl-1-phenyl-cyclohexanol; 4-(4-chlorobenzyl)-1-(4-chlorophenyl)-2-dimethylaminomethyl-cyclohexanol; 4-(4-chlorobenzyl)-2-dimethylaminomethyl-1-(4-fluoro-3-methyl-phenyl)-cyclohexanol; 4-(4-chlorobenzyl)-2-dimethylaminomethyl-1-o-tolyl-cyclohexanol; 4-(4-chlorobenzyl)-2-dimethylaminomethyl-1-vinyl-cyclohexanol; 4-(4-chlorobenzyl)-1-cyclopentyl-2-dimethylaminomethyl-cyclohexanol; 4-(4-chlorobenzyl)-2-dimethylaminomethyl-1-m-tolyl-cyclohexanol; 4-(4-chlorobenzyl)-2-dimethylaminomethyl-bicyclohexyl-1-ol; 4-(4-chlorobenzyl)-2-dimethylaminomethyl-1-(4-fluorophenyl)-cyclohexanol; 4-(4-chlorobenzyl)-2-dimethylaminomethyl-1-phenethyl-cyclohexanol; 4-(4-chlorobenzyl)-2-dimethylaminomethyl-1-phenylethynyl-cyclohexanol; 4-(4-chlorobenzyl)-2-dimethylaminomethyl-1-thiophen-2-yl-cyclohexanol; 4-(4-chlorobenzyl)-2-dimethylaminomethyl-1-p-tolyl-cyclohexanol; 4-(4-chlorobenzyl)-2-dimethylaminomethyl-1-(4-methoxy-phenyl)-cyclohexanol; 4-(4-chlorobenzyl)-2-dimethylaminomethyl-1-trimethylsilanylethynyl-cyclohexanol; 4-(4-chlorobenzyl)-1-(4-chloro-3-trifluoromethyl-phenyl)-2-dimethylaminomethyl-cyclohexanol; 4-(4-chlorobenzyl)-1-(3-chloro-4-fluorophenyl)-2-dimethylaminomethyl-cyclohexanol; 4-(4-chlorobenzyl)-2-dimethylaminomethyl-1-(3-trifluoromethyl-phenyl)-cyclohexanol; 2-dimethylaminomethyl-4-(4-fluorobenzyl)-1-phenyl-cyclohexanol; 1-(4-chlorophenyl)-2-dimethylaminomethyl-4-(4-fluorobenzyl)-cyclohexanol; 1-benzyl-2-dimethylaminomethyl-4-(4-fluorobenzyl)-cyclohexanol; 2-dimethylaminomethyl-4-(4-fluorobenzyl)-1-(4-fluoro-3-methyl-phenyl)-cyclohexanol; 2-dimethylaminomethyl-4-(4-fluorobenzyl)-1-o-tolyl-cyclohexanol; 2-dimethylaminomethyl-4-(4-fluorobenzyl)-1-vinyl-cyclohexanol; 1-(4-tert-butyl-phenyl)-2-dimethylaminomethyl-4-(4-fluorobenzyl)-cyclohexanol; 1-cyclopentyl-2-dimethylaminomethyl-4-(4-fluorobenzyl)-cyclohexanol; 2-dimethylaminomethyl-4-(4-fluorobenzyl)-1-m-tolyl-cyclohexanol; 2-dimethylaminomethyl-4-(4-fluorobenzyl)-bicyclohexyl-1-ol; 2-dimethylaminomethyl-4-(4-fluorobenzyl)-1-(4-fluorophenyl)-cyclohexanol; 2-dimethylaminomethyl-4-(4-fluorobenzyl)-1-phenethyl-cyclohexanol; 2-dimethylaminomethyl-4-(4-fluorobenzyl)-1-phenylethynyl-cyclohexanol; 2-dimethylaminomethyl-4-(4-fluorobenzyl)-1-thiophen-2-yl-cyclohexanol; 2-dimethylaminomethyl-4-(4-fluorobenzyl)-1-(3-methoxy-phenyl)-cyclohexanol; 2-dimethylaminomethyl-4-(4-fluorobenzyl)-1-(3-phenyl-propyl)-cyclohexanol; 1-(2,3-dichlorophenyl)-2-dimethylaminomethyl-4-(4-fluorobenzyl)-cyclohexanol; 2-dimethylaminomethyl-4-(4-fluorobenzyl)-1-p-tolyl-cyclohexanol; 2-dimethylaminomethyl-4-(4-fluorobenzyl)-1-(4-methoxy-phenyl)-cyclohexanol; 1-cyclohexylmethyl-2-dimethylaminomethyl-4-(4-fluorobenzyl)-cyclohexanol; 2-dimethylaminomethyl-4-(4-fluorobenzyl)-1-(5-fluoro2-methoxy-phenyl)-cyclohexanol; 2-dimethylaminomethyl-4-(4-fluorobenzyl)-1-(3-fluorophenyl)-cyclohexanol; 1-(3-chlorophenyl)-2-dimethylaminomethyl-4-(4-fluorobenzyl)-cyclohexanol; 1-(3,5-dichlorophenyl)-2-dimethylaminomethyl-4-(4-fluorobenzyl)-cyclohexanol; 1-(2-chlorobenzyl)-2-dimethylaminomethyl-4-(4-fluorobenzyl)-cyclohexanol; 2-dimethylaminomethyl-1,4-bis-(4-fluorobenzyl)-cyclohexanol; 2-dimethylaminomethyl-4-(4-fluorobenzyl)-1-(3-methoxy-benzyl)-cyclohexanol; 1-(4-chloro-3-trifluoromethyl-phenyl)-2-dimethylaminomethyl-4-(4-fluorobenzyl)-cyclohexanol; 2-dimethylaminomethyl-4-(4-fluorobenzyl)-1-(3-fluorobenzyl)-cyclohexanol; 2-dimethylaminomethyl-4-(4-fluorobenzyl)-1-(2-methoxy-phenyl)-cyclohexanol; 2-dimethylaminomethyl-4-(4-fluorobenzyl)-1-(2-methyl-benzyl)-cyclohexanol; 1-(3-chloro-4-fluorophenyl)-2-dimethylaminomethyl-4-(4-fluorobenzyl)-cyclohexanol; 2-dimethylaminomethyl-4-(4-fluorobenzyl)-1-(3-trifluoromethyl-phenyl)-cyclohexanol; 2-dimethylaminomethyl-4-(4-fluorobenzyl)-1-(3-methyl-benzyl)-cyclohexanol; 1-(4-chlorobenzyl)-2-dimethylaminomethyl-4-(4-fluorobenzyl)-cyclohexanol; 1-(2-chloro-6-fluorobenzyl)-2-dimethylaminomethyl-4-(4-fluorobenzyl)-cyclohexanol; 2-dimethylaminomethyl-1-(2,5-dimethyl-benzyl)-4-(4-fluorobenzyl)-cyclohexanol; 1-(3-chlorobenzyl)-2-dimethylaminomethyl-4-(4-fluorobenzyl)-cyclohexanol; 1-(2,4-dichlorobenzyl)-2-dimethylaminomethyl-4-(4-fluorobenzyl)-cyclohexanol; 2-dimethylaminomethyl-4-(3-methoxy-benzyl)-1-phenyl-cyclohexanol; 1-benzyl-2-dimethylaminomethyl-4-(3-methoxy-benzyl)-cyclohexanol; 2-dimethylaminomethyl-1-(4-fluoro-3-methyl-phenyl)-4-(3-methoxy-benzyl)-cyclohexanol; 2-dimethylaminomethyl-4-(3-methoxy-benzyl)-1-o-tolyl-cyclohexanol; 2-dimethylaminomethyl-4-(3-methoxy-benzyl)-1-vinyl-cyclohexanol; 1-(4-tert-butyl-phenyl)-2-dimethylaminomethyl-4-(3-methoxy-benzyl)-cyclohexanol; 1-cyclopentyl-2-dimethylaminomethyl-4-(3-methoxy-benzyl)-cyclohexanol; 2-dimethylaminomethyl-4-(3-methoxy-benzyl)-1-m-tolyl-cyclohexanol; 2-dimethylaminomethyl-4-(3-methoxy-benzyl)-bicyclohexyl-1-ol; 2-dimethylaminomethyl-4-(3-methoxy-benzyl)-1-phenethyl-cyclohexanol; 2-dimethylaminomethyl-4-(3-methoxy-benzyl)-1-phenylethynyl-cyclohexanol; 2-dimethylaminomethyl-4-(3-methoxy-benzyl)-1-thiophen-2-yl-cyclohexanol; 2-dimethylaminomethyl-4-(3-methoxy-benzyl)-1-(3-methoxy-phenyl)-cyclohexanol; 2-dimethylaminomethyl-4-(3-methoxy-benzyl)-1-(3-phenyl-propyl)-cyclohexanol; 1-(2,3-dichlorophenyl)-2-dimethylaminomethyl-4-(3-methoxy-benzyl)-cyclohexanol; 2-dimethylaminomethyl-4-(3-methoxy-benzyl)-1-p-tolyl-cyclohexanol; 1-cyclohexylmethyl-2-dimethylaminomethyl-4-(3-methoxy-benzyl)-cyclohexanol; 2-dimethylaminomethyl-1-(5-fluoro-2-methoxy-phenyl)-4-(3-methoxy-benzyl)-cyclohexanol; 1-(3-chlorophenyl)-2-dimethylaminomethyl-4-(3-methoxy-benzyl)-cyclohexanol; 1-(3,5-dichlorophenyl)-2-dimethylaminomethyl-4-(3-methoxy-benzyl)-cyclohexanol; 1-(4-chloro-3-trifluoromethyl-phenyl)-2-dimethylaminomethyl-4-(3-methoxybenzyl)-cyclohexanol; 2-dimethylaminomethyl-1-(3-fluorobenzyl)-4-(3-methoxy-benzyl)-cyclohexanol; 2-dimethylaminomethyl-4-(3-methoxy-benzyl)-1-(2-methoxy-phenyl)-cyclohexanol; 2-dimethylaminomethyl-4-(3-methoxy-benzyl)-1-(3-trifluoromethyl-phenyl)-cyclohexanol; 1-(2-chloro-6-fluorobenzyl)-2-dimethylaminomethyl-4-(3-methoxy-benzyl)-cyclohexanol; 2-dimethylaminomethyl-1-(2,5-dimethyl-benzyl)-4-(3-methoxy-benzyl)-cyclohexanol; 1-(3-chlorobenzyl)-2-dimethylaminomethyl-4-(3-methoxy-benzyl)-cyclohexanol; 2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-1-phenyl-cyclohexanol; 1-benzyl-2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-cyclohexanol; 2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-1-(4-fluoro-3-methyl-phenyl)-cyclohexanol; 2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-1-vinyl-cyclohexanol; 1-(4-tert-butyl-phenyl)-2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-cyclohexanol; 1-cyclopentyl-2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-cyclohexanol; 2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-1-m-tolyl-cyclohexanol; 2-dimethylaminomethyl-4-(4-fluorobenzyloxy)bicyclohexyl-1-ol; 2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-1-phenethyl-cyclohexanol; 2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-1-phenylethynyl-cyclohexanol; 2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-1-thiophen-2-yl-cyclohexanol; 2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-1-(3-methoxy-phenyl)-cyclohexanol; 2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-1-p-tolyl-cyclohexanol; 1-cyclohexylmethyl-2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-cyclohexanol; 2-dimethylaminomethyl-1-(3-fluorobenzyl)-4-(4-fluorobenzyloxy)-cyclohexanol; 2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-1-(2-methoxy-phenyl)-cyclohexanol; 2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-1-(3-methyl-benzyl)-cyclohexanol; 2-dimethylaminomethyl-1-(2,5-dimethyl-benzyl)-4-(4-fluorobenzyloxy)-cyclohexanol; 1-(3-chlorobenzyl)-2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-cyclohexanol; [5-benzyloxy-2-(3-methoxy-phenyl)-cyclohexylmethyl]-dimethyl-amine; [5-(3-chlorobenzyloxy)-2-(3-methoxy-phenyl)-cyclohexylmethyl]-dimethyl-amine; [2-(3-methoxy-phenyl)-5-(naphthalen-2-ylmethoxy)-cyclohexylmethyl]-dimethylamine; [5-(3-methoxy-benzyloxy)-2-(3-methoxy-phenyl)-cyclohexylmethyl]-dimethylamine; [5-(4-chlorobenzyloxy)-2-(3-methoxy-phenyl)-cyclohexylmethyl]-dimethyl-amine; [5-(4-methoxy-benzyloxy)-2-(3-methoxy-phenyl)-cyclohexylmethyl]-dimethylamine; 2-dimethylaminomethyl-1-(3-methoxy-phenyl)-4-(naphthalen-2-ylmethoxy)-cyclohexanol; [5-(4-methoxy-benzyloxy)-2-(3-methoxy-phenyl)-cyclohex-2-enylmethyl]dimethyl-amine; butyric acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexylester; 4-amino-2-dimethylaminomethyl-1-(3-methoxy-phenyl)-cyclohexanol; 2-dimethylaminomethyl-1-(3-methoxy-phenyl)-4-(naphthalen-2-ylmethoxy)-cyclohexanol; 4-methoxy-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxyphenyl)-cyclohexylester; 3-methoxy-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxyphenyl)-cyclohexylester; 2,2-dimethyl-propionic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxyphenyl)-cyclohexylester; butyric acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexylester; 4-methoxy-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxyphenyl)-cyclohexylester; 3-methoxy-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxyphenyl)-cyclohexylester; 2,2-dimethyl-propionic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxyphenyl)-cyclohexylester; 3,4-dimethoxy-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxyphenyl)-cyclohexylester; 3,4-dimethoxy-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxyphenyl)-cyclohexylester; naphthalene-2-carboxylic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxyphenyl)-cyclohexylester; 4-methyl-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexylester; 3,4-dichloro-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxyphenyl)-cyclohexylester; 4-chloro-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexylester; 3-chloro-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexylester; 2-chloro-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexylester; 4-trifluoromethyl-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexylester; 3,5-difluoro-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxyphenyl)-cyclohexylester; 4-fluoro-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexylester; 3-fluoro-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexylester; 2-fluoro-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexylester; cyclopentanecarboxylic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxyphenyl)-cyclohexylester; (4-methoxy-phenyl)-acetic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexylester; (3-methoxy-phenyl)-acetic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexylester; phenyl-acetic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexylester; 3,4,5-trimethoxy-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexylester; 3,5-dimethoxy-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxyphenyl)-cyclohexylester; naphthalene-1-carboxylic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxyphenyl)-cyclohexylester; 2-methoxy-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxyphenyl)-cyclohexylester; naphthalene-2-carboxylic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxyphenyl)-cyclohexylester; 2-hydroxy-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxyphenyl)-cyclohexylester; 4-methyl-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexylester; 3,4-dichloro-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxyphenyl)-cyclohexylester; 4-chloro-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexylester; 3-chloro-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexylester; 2-chloro-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexylester; 4-trifluoromethyl-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexylester; 3,5-difluoro-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxyphenyl)-cyclohexylester; 4-fluoro-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexylester; 3-fluoro-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexylester; 2-fluoro-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexylester; cyclopentanecarboxylic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxyphenyl)-cyclohexylester; (4-methoxy-phenyl)-acetic acid 3-dimethylaminomethyl-4-hydroxy-3234-(3-methoxy-phenyl)-cyclohexylester; (3-methoxy-phenyl)-acetic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexylester; phenyl-acetic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexylester; 3,4,5-trimethoxy-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexylester; 3,5-dimethoxy-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxyphenyl)-cyclohexylester; naphthalene-1-carboxylic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxyphenyl)-cyclohexylester; 2-methoxy-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxyphenyl)-cyclohexylester; 2-dimethylaminomethyl-1,4-bis-(3-methoxy-phenyl)-cyclohexane-1,4-diol; 2-dimethylaminomethyl-1,4-bis-(3-methoxy-phenyl)-cyclohexane-1,4-diol; 6-(4-benzyloxy-2-dimethylaminomethyl-1-hydroxy-cyclohexyl)-naphthalen-2-ol; 4-benzyloxy-2-dimethylaminomethyl-1-(6-methoxy-naphthalen-2-yl)-cyclohexanol; butyric acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexylester; butyric acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexylester; 2-dimethylaminomethyl-1-(3-methoxy-phenyl)-4-methylamino-cyclohexanol; 2-dimethylaminomethyl-1-(3-methoxy-phenyl-4-methylamino-cyclohexanol; valeric acid 3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexylester; [3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexylidene] acetic acid ethylester; [3-dimethylaminomethyl-4-hydroxy-4-(3-methoxy-phenyl)-cyclohexylidene] acetic acid ethylester; 3-[2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-1-hydroxy-cyclohexyl]-phenol; 4-benzyloxy-2-dimethylaminomethyl-1-(3-phenyl-propyl)-cyclohexanol; 2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-1-(3-phenyl-propyl)-cyclohexanol; 2-dimethylaminomethyl-1-(3-fluorobenzyl)-4-(4-fluorobenzyloxy)-cyclohexanol; 4-benzyloxy-2-dimethylaminomethyl-1-(3-fluorobenzyl)-cyclohexanol; 2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-1-p-tolyl-cyclohexanol; 4-benzyloxy-2-dimethylaminomethyl-1-p-tolyl-cyclohexanol; 2-dimethylaminomethyl-1-(2,5-dimethyl-benzyl)-4-(4-fluorobenzyloxy)-cyclohexanol; 4-benzyloxy-2-dimethylaminomethyl-1-(2,5-dimethyl-benzyl)-cyclohexanol; 1-(4-chloro-3-trifluoromethyl-phenyl)-2-dimethylaminomethyl-4-(4-fluorbenzyloxy)-cyclohexanol; 4-benzyloxy-1-(4-chloro-3-trifluoromethyl-phenyl)-2-dimethylaminomethylcyclohexanol; [2,5-bis-(4-fluorobenzyloxy)-2-(3-methoxy-phenyl)-cyclohexylmethyl]-dimethylamine; 5-dimethylaminomethyl-4-(3-methoxy-phenyl)-cyclohex-3-enol; 2-dimethylaminomethyl-1-(6-methoxynaphthalen-2-yl)-cyclohexane-1,4-diol; butyric acid 3-dimethylaminomethyl-4-hydroxy-4-(6-methoxynaphthalen-2-yl)-cyclohexylester; benzoic acid 4-hydroxy-3-(4-methyl-piperazin-1-ylmethyl)-4-naphthalen-2-ylcyclohexyl ester; 2-chloro-benzoic acid 4-hydroxy-3-(4-methyl-piperazin-1-ylmethyl)-4-naphthalen-2-yl-cyclohexyl ester; 3-chloro-benzoic acid 4-hydroxy-3-(4-methyl-piperazin-1-ylmethyl)-4-naphthalen-2-yl-cyclohexyl ester; 4-chloro-benzoic acid 4-hydroxy-3-(4-methyl-piperazin-1-ylmethyl)-4-naphthalen-2-yl-cyclohexyl ester; 2-fluoro-benzoic acid 4-hydroxy-3-(4-methyl-piperazin-1-ylmethyl)-4-naphthalen-2-yl-cyclohexyl ester; 3-fluoro-benzoic acid 4-hydroxy-3-(4-methyl-piperazin-1-ylmethyl)-4-naphthalen-2-yl-cyclohexyl ester; 4-fluoro-benzoic acid 4-hydroxy-3-(4-methyl-piperazin-1-ylmethyl)-4-naphthalen-2-yl-cyclohexyl ester; 2-methyl-benzoic acid 4-hydroxy-3-(4-methyl-piperazin-1-ylmethyl)-4-naphthalen-2-yl-cyclohexyl ester; 3-methyl-benzoic acid 4-hydroxy-3-(4-methyl-piperazin-1-ylmethyl)-4-naphthalen-2-yl-cyclohexyl ester; 4-methyl-benzoic acid 4-hydroxy-3-(4-methyl-piperazin-1-ylmethyl)-4-naphthalen-2-yl-cyclohexyl ester; 2-methoxy-benzoic acid 4-hydroxy-3-(4-methyl-piperazin-1-ylmethyl)-4naphthalen-2-yl-cyclohexyl ester; 3-methoxy-benzoic acid 4-hydroxy-3-(4-methyl-piperazin-1-ylmethyl)-4naphthalen-2-yl-cyclohexyl ester; 4-methoxy-benzoic acid 4-hydroxy-3-(4-methyl-piperazin-1-ylmethyl)-4naphthalen-2-yl-cyclohexyl ester; 2,6-dichloro-benzoic acid 4-hydroxy-3-(4-methyl-piperazin-1-ylmethyl)-4naphthalen-2-yl-cyclohexyl ester; 2,6-difluoro-benzoic acid 4-hydroxy-3-(4-methyl-piperazin-1-ylmethyl)-4naphthalen-2-yl-cyclohexyl ester; 2-chloro5-fluoro-benzoic acid 4-hydroxy-3-(4-methyl-piperazin-1-ylmethyl)-4naphthalen-2-yl-cyclohexyl ester; biphenyl-4-carboxylic acid 4-hydroxy-3-(4-methyl-piperazin-1-ylmethyl)-4-naphthalen-2-yl-cyclohexylester; 2-chloro-benzoic acid 4-hydroxy-4-(6-methoxy-naphthalen-2-yl)-3-(4-methyl piperazin-1-ylmethyl)-cyclohexyl ester; 3-chloro-benzoic acid 4-hydroxy-4-(6-methoxy-naphthalen-2-yl)-3-(4-methyl-piperazin-1-ylmethyl)-cyclohexyl ester; 4-chloro-benzoic acid 4-hydroxy-4-(6-methoxy-naphthalen-2-yl)-3-(4-methyl-piperazin-1-ylmethyl)-cyclohexyl ester; 2-fluoro-benzoic acid 4-hydroxy-4-(6-methoxy-naphthalen-2-yl)-3-(4-methyl-piperazin-1-ylmethyl)-cyclohexyl ester; 3-fluoro-benzoic acid 4-hydroxy-4-(6-methoxy-naphthalen-2-yl)-3-(4-methyl piperazin-1-ylmethyl)-cyclohexyl ester; 4-fluoro-benzoic acid 4-hydroxy-4-(6-methoxy-naphthalen-2-yl)-3-(4-methyl piperazin-1-ylmethyl)-cyclohexyl ester; 2-methyl-benzoic acid 4-hydroxy-4-(6-methoxy-naphthalen-2-yl)-3-(4-methyl-piperazin-1-ylmethyl)-cyclohexyl ester; 3-methyl-benzoic acid 4-hydroxy-4-(6-methoxy-naphthalen-2-yl)-3-(4-methyl-piperazin-1-ylmethyl)-cyclohexyl ester; 4-methyl-benzoic acid 4-hydroxy-4-(6-methoxy-naphthalen-2-yl)-3-(4-methyl-piperazin-1-ylmethyl)-cyclohexyl ester; 2-methoxy-benzoic acid 4-hydroxy-4-(6-methoxy-naphthalen-2-yl).-3-(4-methyl-piperazin-1-ylmethyl)-cyclohexyl ester; 3-methoxy-benzoic acid 4-hydroxy-4-(6-methoxy-naphthalen-2-yl)-3-(4-methyl-piperazin-1-ylmethyl)-cyclohexyl ester; 4-methoxy-benzoic acid 4-hydroxy-4-(6-methoxy-naphthalen-2-yl)-3-(4-methyl-piperazin-1-ylmethyl)-cyclohexyl ester; 2,6-dichloro-benzoic acid 4-hydroxy-4-(6-methoxy-naphthalen-2-yl)-3-(4-methyl-piperazin-1-ylmethyl)-cyclohexyl ester; 2,6-fluoro-benzoic acid 4-hydroxy-4-(6-methoxy-naphthalen-2-yl)-3-(4-methyl piperazin-1-ylmethyl)-cyclohexyl ester; 2-chloro-6-fluoro-benzoic acid 4-hydroxy-4-(6-methoxy-naphthalen-2-yl)-3-(4methyl-piperazin-1-ylmethyl)-cyclohexyl ester; biphenyl-4-carboxylic acid 4-hydroxy-4-(6-methoxy-naphthalen-2-yl)-3-(4-methyl-piperazin-1-ylmethyl)-cyclohexyl ester; 4-(2-chlorobenzyloxy)-2-(4-methyl-piperazin-1-ylmethyl)-1-naphthalen-2-yl-cyclohexanol; 4-(3-chlorobenzyloxy)-2-(4-methyl-piperazin-1-ylmethyl)-1-naphthalen-2-yl-cyclohexanol; 4-(4-chlorobenzyloxy)-2-(4-methyl-piperazin-1-ylmethyl)-1-naphthalen-2-yl-cyclohexanol; 4-(2-fluorobenzyloxy)-2-(4-methyl-piperazin-1-ylmethyl)-1-naphthalen-2-yl-cyclohexanol; 4-(3-fluorobenzyloxy)-2-(4-methyl-piperazin-1-ylmethyl)-1-naphthalen-2-yl-cyclohexanol; 4-(4-fluorobenzyloxy)-2-(4-methyl-piperazin-1-ylmethyl)-1-naphthalen-2-yl-cyclohexanol; 4-(2-methyl-benzyloxy)-2-(4-methyl-piperazin-1-ylmethyl)-1-naphthalen-2-ylcyclohexanol; 4-(3-methyl-benzyloxy)-2-(4-methyl-piperazin-1-ylmethyl)-1-naphthalen-2-ylcyclohexanol; 4-(4-methyl-benzyloxy)-2-(4-methyl-piperazin-1-ylmethyl)-1-naphthalen-2-ylcyclohexanol; 4-(2-methoxy-benzyloxy)-2-(4-methyl-piperazin-1-ylmethyl)-1-naphthalen-2-ylcyclohexanol; 4-(3-methoxy-benzyloxy)-2-(4-methyl-piperazin-1-ylmethyl)-1-naphthalen-2-ylcyclohexanol; 4-(4-methoxy-benzyloxy)-2-(4-methyl-piperazin-1-ylmethyl)-1-naphthalen-2-ylcyclohexanol; 4-(2,6-dichlorobenzyloxy)-2-(4-methyl-piperazin-1-ylmethyl)-1-naphthalen-2-ylcyclohexanol; 4-(2,6-difluorobenzyloxy)-2-(4-methyl-piperazin-1-ylmethyl)-1-naphthalen-2-ylcyclohexanol; 4-(2-chloro-6-fluorobenzyloxy)-2-(4-methyl-piperazin-1-ylmethyl)-1-naphthalen-2-yl-cyclohexanol; 4-(2-chlorobenzyloxy)-1-(6-methoxy-naphthalen-2-yl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclohexanol; 4-(3-chlorobenzyloxy)-1-(6-methoxy-naphthalen-2-yl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclohexanol; 4-(4-chlorobenzyloxy)-1-(6-methoxy-naphthalen-2-yl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclohexanol; 4-(2-fluorobenzyloxy)-1-(6-methoxy-naphthalen-2-yl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclohexanol; 4-(3-fluorobenzyloxy)-1-(6-methoxy-naphthalen-2-yl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclohexanol; 4-(4-fluorobenzyloxy)-1-(6-methoxy-naphthalen-2-yl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclohexanol; 4-(2-methyl-benzyloxy)-1-(6-methoxy-naphthalen-2-yl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclohexanol; 4-(3-methyl-benzyloxy)-1-(6-methoxy-naphthalen-2-yl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclohexanol; 4-(4-methyl-benzyloxy)-1-(6-methoxy-naphthalen-2-yl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclohexanol; 4-(2-methoxy-benzyloxy)-1-(6-methoxy-naphthalen-2-yl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclohexanol; 4-(3-methoxy-benzyloxy)-1-(6-methoxy-naphthalen-2-yl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclohexanol; 4-(4-methoxy-benzyloxy)-1-(6-methoxy-naphthalen-2-yl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclohexanol; 4-(2,6-dichlorobenzyloxy)-1-(6-methoxy-naphthalen-2-yl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclohexanol; 4-(2,6-difluorobenzyloxy)-1-(6-methoxy-naphthalen-2-yl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclohexanol; 4-(2-chloro-6-fluorobenzyloxy)-1-(6-methoxy-naphthalen-2-yl)-2-(4-methyl-piperazin-1-ylmethyl)-cyclohexanol; 2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-1-naphthalen-2-yl-cyclohexanol; 4-fluoro-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-(6-methoxy-naphthalen-2-yl)-cyclohexylester; 4-fluoro-benzoic acid 3-dimethylaminomethyl-4-hydroxy-4-naphthalen-2-ylcyclohexylester; 2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-1-(6-methoxy-naphthalen-2-yl)-cyclohexanol; and 6-[2-dimethylaminomethyl-4-(4-fluorobenzyloxy)-1-hydroxy-cyclohexyl]naphthalen-2-ol.
 51. A pharmaceutical composition comprising at least one compound according to claim 1, and a pharmaceutically acceptable excipient.
 52. A pharmaceutical composition according to claim 51, wherein the compound is in the form of a pure diastereomer or enantiomer.
 53. A pharmaceutical composition according to claim 51, wherein the compound is in the form of a racemate or equimolar mixture of diastereomers.
 54. A pharmaceutical composition according to claim 51, wherein the compound is in the form of a non-equimolar mixture of enatiomers or non-equimolar mixture of diastereomers.
 55. A method for the treatment of pain, comprising administering an effective amount of a pharmaceutical composition according to claim 51 to a patient in need thereof.
 56. A method according to claim 55, wherein the pain is neuropathic or chronic pain. 